Butyrolactones as herbicides

ABSTRACT

Disclosed are compounds of Formula 1, including all stereoisomers, N-oxides, and salts thereof, 
     
       
         
         
             
             
         
       
     
     wherein R 1 , R 2 , R 3 , R 4 , R 5 , Q 1 , Q 2 , Y 1 , and Y 2  are as defined in the disclosure. 
     Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling undesired vegetation comprising contacting the undesired vegetation or its environment with an effective amount of a compound or a composition of the invention.

FIELD OF THE INVENTION

This invention relates to certain butyrolactones, their N-oxides, saltsand compositions, and methods of their use for controlling undesirablevegetation.

BACKGROUND OF THE INVENTION

The control of undesired vegetation is extremely important in achievinghigh crop efficiency. Achievement of selective control of the growth ofweeds especially in such useful crops as rice, soybean, sugar beet,maize, potato, wheat, barley, tomato and plantation crops, among others,is very desirable. Unchecked weed growth in such useful crops can causesignificant reduction in productivity and thereby result in increasedcosts to the consumer. The control of undesired vegetation in noncropareas is also important. Many products are commercially available forthese purposes, but the need continues for new compounds that are moreeffective, less costly, less toxic, environmentally safer or havedifferent sites of action.

SUMMARY OF THE INVENTION

This invention is directed to a compound of Formula 1 (including allstereoisomers), including N-oxides and salts thereof, agriculturalcompositions containing them and their use as herbicides:

wherein

-   -   Q¹ is a phenyl ring or a naphthalenyl ring system, each ring or        ring system optionally substituted with up to 5 substituents        independently selected from R⁷; or a 5- to 6-membered fully        unsaturated heterocyclic ring or an 8- to 10-membered        heteroaromatic bicyclic ring system, each ring or ring system        containing ring members selected from carbon atoms and 1 to 4        heteroatoms independently selected from up to 2 O, up to 2 S and        up to 4 N atoms, wherein up to 3 carbon ring members are        independently selected from C(═O) and C(═S), and the sulfur atom        ring members are independently selected from        S(═O)_(u)(═NR⁸)_(v), each ring or ring system optionally        substituted with up to 5 substituents independently selected        from R⁷ on carbon atom ring members and selected from R⁹ on        nitrogen atom ring members;    -   Q² is a phenyl ring or a naphthalenyl ring system, each ring or        ring system optionally substituted with up to 5 substituents        independently selected from R¹⁰; or a 5- to 6-membered fully        unsaturated heterocyclic ring or an 8- to 10-membered        heteroaromatic bicyclic ring system, each ring or ring system        containing ring members selected from carbon atoms and 1 to 4        heteroatoms independently selected from up to 2 O, up to 2 S and        up to 4 N atoms, wherein up to 3 carbon ring members are        independently selected from C(═O) and C(═S), and the sulfur atom        ring members are independently selected from        S(═O)_(u)(═NR⁸)_(v), each ring or ring system optionally        substituted with up to 8 substituents independently selected        from R¹⁰ on carbon atom ring members and selected from R¹¹ on        nitrogen atom ring members;    -   Y¹ and Y² are each independently O, S or NR⁶;    -   R¹ is H, hydroxy, amino, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆        alkenyl, C₃-C₆ alkynyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈ alkylsulfinylalkyl,        C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈        haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈        alkoxycarbonyl, C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀        cycloalkoxycarbonyl, C₂-C₈ alkylaminocarbonyl, C₃-C₁₀        dialkylaminocarbonyl, C₄-C₁₀ cycloalkylaminocarbonyl, C₁-C₆        alkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio, C₃-C₈        cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl,        C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆        alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀        trialkylsilyl or G¹;    -   R² and R³ are each independently H, halogen, hydroxy, C₁-C₄        alkyl, C₁-C₄ haloalkyl or C₁-C₄ alkoxy; or    -   R² and R³ are taken together with the carbon atom to which they        are bonded to form a C₃-C₇ cycloalkyl ring;    -   R⁴ and R⁵ are each independently H, halogen, hydroxy, C₁-C₄        alkyl or C₁-C₄ alkoxy; each R⁶ is independently H, cyano, C₁-C₄        alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,        —(C═O)CH₃ or —(C═O)CF₃;    -   each R⁸ is independently H, cyano, C₂-C₃ alkylcarbonyl or C₂-C₃        haloalkylcarbonyl;    -   each R⁷ and R¹⁰ is independently halogen, cyano, nitro, C₁-C₈        alkyl, C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl,        C₁-C₈ nitroalkyl, C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈        nitroalkenyl, C₂-C₈ alkynyl, C₂-C₈ haloalkynyl, C₄-C₁₀        cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl, C₅-C₁₂        alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂        cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl,        C₄-C₁₀ alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈        cycloalkenyl, C₃-C₈ halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈        haloalkoxyalkyl, C₄-C₁₀ cycloalkoxyalkyl, C₃-C₁₀        alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈        alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈        alkylaminoalkyl, C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀        cycloalkylaminoalkyl, C₃-C₁₀ dialkylaminoalkyl, —CHO, C₂-C₈        alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₄-C₁₀        cycloalkylcarbonyl, —C(═O)OH, C₂-C₈ alkoxycarbonyl, C₂-C₈        haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂        cycloalkylalkoxycarbonyl, —C(═O)NH₂, C₂-C₈ alkylaminocarbonyl,        C₄-C₁₀ cycloalkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl,        C₁-C₈ alkoxy, C₁-C₈ haloalkoxy, C₂-C₈ alkoxyalkoxy, C₂-C₈        haloalkoxyalkoxy, C₂-C₈ alkenyloxy, C₂-C₈ haloalkenyloxy, C₃-C₈        alkynyloxy, C₃-C₈ haloalkynyloxy, C₃-C₈ cycloalkoxy, C₃-C₈        halocycloalkoxy, C₄-C₁₀ cycloalkylalkoxy, C₃-C₁₀        alkylcarbonylalkoxy, C₂-C₈ alkylcarbonyloxy, C₂-C₈        haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₁-C₈        alkylsulfonyloxy, C₁-C₈ haloalkylsulfonyloxy, C₁-C₈ alkylthio,        C₁-C₈ haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₈ alkylsulfinyl,        C₁-C₈ haloalkylsulfinyl, C₁-C₈ alkylsulfonyl, C₁-C₈        haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, formylamino, C₂-C₈        alkylcarbonylamino, C₂-C₈ haloalkylcarbonylamino, C₂-C₈        alkoxycarbonylamino, C₁-C₆ alkylsulfonylamino, C₁-C₆        haloalkylsulfonylamino, —SF₅, —SCN, SO₂NH₂, C₃-C₁₂        trialkylsilyl, C₄-C₁₂ trialkylsilylalkyl, C₄-C₁₂        trialkylsilylalkoxy or G²; or    -   two adjacent R⁷ are taken together along with the carbon atoms        to which they are bonded to form a C₃-C₇ cycloalkyl ring; or    -   two adjacent R¹⁰ are taken together along with the carbon atoms        to which they are bonded to form a C₃-C₇ cycloalkyl ring;    -   each R⁹ and R¹¹ is independently cyano, C₁-C₃ alkyl, C₂-C₃        alkenyl, C₂-C₃ alkynyl, C₃-C₆ cycloalkyl, C₂-C₃ alkoxyalkyl,        C₁-C₃ alkoxy, C₂-C₃ alkylcarbonyl, C₂-C₃ alkoxycarbonyl, C₂-C₃        alkylaminoalkyl or C₃-C₄ dialkylaminoalkyl;    -   each G¹ is independently phenyl, phenylmethyl (i.e. benzyl),        pyridinylmethyl, phenylcarbonyl (i.e. benzoyl),        phenylcarbonyl(C₁-C₄ alkyl), phenoxy, phenylethynyl,        phenylsulfonyl, or a 5- or 6-membered heteroaromatic ring, each        optionally substituted on ring members with up to 5 substituents        independently selected from R¹²;    -   each G² is independently phenyl, phenylmethyl (i.e. benzyl),        pyridinylmethyl, phenylcarbonyl (i.e. benzoyl),        phenylcarbonyl(C₁-C₄ alkyl), phenoxy, phenylethynyl,        phenylsulfonyl, pyridinyloxy, or a 5- or 6-membered        heteroaromatic ring, each optionally substituted on ring members        with up to 5 substituents independently selected from R¹³;    -   each R¹² and R¹³ is independently halogen, cyano, hydroxy,        amino, nitro, —CHO, —C(═O)OH, —C(═O)NH₂, —SO₂NH₂, C₁-C₆ alkyl,        C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₂-C₈        alkylcarbonyl, C₂-C₈ haloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,        C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl,        C₂-C₈ alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₁-C₆        alkoxy, C₁-C₆ haloalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆        alkylthio, C₁-C₆ haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆        haloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylsulfonyl,        C₁-C₆ alkylaminosulfonyl, C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀        trialkylsilyl, C₁-C₆ alkylamino, C₂-C₈ dialkylamino, C₂-C₈        alkylcarbonylamino, C₁-C₆ alkylsulfonylamino, phenyl, pyridinyl        or thienyl; and    -   each u and v are independently 0, 1 or 2 in each instance of        S(═O)_(u)(═NR⁸)_(v), provided that the sum of u and v is 0, 1 or        2.

More particularly, this invention pertains to a compound of Formula 1(including all stereoisomers), an N-oxide or a salt thereof. Thisinvention also relates to a herbicidal composition comprising a compoundof the invention (i.e. in a herbicidally effective amount) and at leastone component selected from the group consisting of surfactants, soliddiluents and liquid diluents. This invention further relates to a methodfor controlling the growth of undesired vegetation comprising contactingthe vegetation or its environment with a herbicidally effective amountof a compound of the invention (e.g., as a composition describedherein).

This invention also includes a herbicidal mixture comprising (a) acompound selected from Formula 1, N-oxides, and salts thereof, and (b)at least one additional active ingredient selected from (b1) through(b16); and salts of compounds of (b1) through (b16), as described below.

DETAILS OF THE INVENTION

As used herein, the terms “comprises,” “comprising,” “includes,”“including,” “has,” “having,” “contains”, “containing,” “characterizedby” or any other variation thereof, are intended to cover anon-exclusive inclusion, subject to any limitation explicitly indicated.For example, a composition, mixture, process or method that comprises alist of elements is not necessarily limited to only those elements butmay include other elements not expressly listed or inherent to suchcomposition, mixture, process or method.

The transitional phrase “consisting of” excludes any element, step, oringredient not specified. If in the claim, such would close the claim tothe inclusion of materials other than those recited except forimpurities ordinarily associated therewith. When the phrase “consistingof” appears in a clause of the body of a claim, rather than immediatelyfollowing the preamble, it limits only the element set forth in thatclause; other elements are not excluded from the claim as a whole.

The transitional phrase “consisting essentially of” is used to define acomposition or method that includes materials, steps, features,components, or elements, in addition to those literally disclosed,provided that these additional materials, steps, features, components,or elements do not materially affect the basic and novelcharacteristic(s) of the claimed invention. The term “consistingessentially of” occupies a middle ground between “comprising” and“consisting of”.

Where applicants have defined an invention or a portion thereof with anopen-ended term such as “comprising,” it should be readily understoodthat (unless otherwise stated) the description should be interpreted toalso describe such an invention using the terms “consisting essentiallyof” or “consisting of.”

Further, unless expressly stated to the contrary, “or” refers to aninclusive or and not to an exclusive or. For example, a condition A or Bis satisfied by any one of the following: A is true (or present) and Bis false (or not present), A is false (or not present) and B is true (orpresent), and both A and B are true (or present).

Also, the indefinite articles “a” and “an” preceding an element orcomponent of the invention are intended to be nonrestrictive regardingthe number of instances (i.e. occurrences) of the element or component.Therefore “a” or “an” should be read to include one or at least one, andthe singular word form of the element or component also includes theplural unless the number is obviously meant to be singular.

As referred to herein, the term “seedling”, used either alone or in acombination of words means a young plant developing from the embryo of aseed.

As referred to herein, the term “broadleaf” used either alone or inwords such as “broadleaf weed” means dicot or dicotyledon, a term usedto describe a group of angiosperms characterized by embryos having twocotyledons.

In the above recitations, the term “alkyl”, used either alone or incompound words such as “alkylthio” or “haloalkyl” includesstraight-chain or branched alkyl, such as, methyl, ethyl, n-propyl,i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl”includes straight-chain or branched alkenes such as ethenyl, 1-propenyl,2-propenyl, and the different butenyl, pentenyl and hexenyl isomers.“Alkenyl” also includes polyenes such as 1,2-propadienyl and2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynessuch as ethynyl, 1-propynyl, 2-propynyl and the different butynyl,pentynyl and hexynyl isomers. “Alkynyl” can also include moietiescomprised of multiple triple bonds such as 2,5-hexadiynyl.

“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy,isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.“Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of“alkoxyalkyl” include CH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂and CH₃CH₂OCH₂CH₂. “Alkoxyalkoxy” denotes alkoxy substitution on alkoxy.“Alkenyloxy” includes straight-chain or branched alkenyloxy moieties.Examples of “alkenyloxy” include H₂C═CHCH₂O, (CH₃)₂C═CHCH₂O,(CH₃)CH═CHCH₂O, (CH₃)CH═C(CH₃)CH₂O and CH₂═CHCH₂CH₂O. “Alkynyloxy”includes straight-chain or branched alkynyloxy moieties. Examples of“alkynyloxy” include HC≡CCH₂O, CH₃C≡CCH₂O and CH₃C≡CCH₂CH₂O. “Alkylthio”includes branched or straight-chain alkylthio moieties such asmethylthio, ethylthio, and the different propylthio, butylthio,pentylthio and hexylthio isomers. “Alkylsulfinyl” includes bothenantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl”include CH₃S(O)—, CH₃CH₂S(O)—, CH₃CH₂CH₂S(O)—, (CH₃)₂CHS(O)— and thedifferent butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers.Examples of “alkylsulfonyl” include CH₃S(O)₂—, CH₃CH₂S(O)₂—,CH₃CH₂CH₂S(O)₂—, (CH₃)₂CHS(O)₂—, and the different butylsulfonyl,pentylsulfonyl and hexylsulfonyl isomers. “Alkylthioalkyl” denotesalkylthio substitution on alkyl. Examples of “alkylthioalkyl” includeCH₃SCH₂, CH₃SCH₂CH₂, CH₃CH₂SCH₂, CH₃CH₂CH₂CH₂SCH₂ and CH₃CH₂SCH₂CH₂.“Cyanoalkyl” denotes an alkyl group substituted with one cyano group.Examples of “cyanoalkyl” include NCCH₂, NCCH₂CH₂ and CH₃CH(CN)CH₂.“Alkylamino”, “dialkylamino”, and the like, are defined analogously tothe above examples. The terms “alkylthioalkyl”, “alkylsulfinylamino”,“alkylsulfonylamino”, “alkylaminosulfonyl”, “alkylsulfonylamino”,“alkylaminoalkyl”, “alkylthioalkyl”, “alkylsulfinylalkyl”,“alkylsulfonylalkyl”, “dialkylaminoalkyl” are defined likewise.

“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyland cyclohexyl. The term “alkylcycloalkyl” denotes alkyl substitution ona cycloalkyl moiety and includes, for example, ethylcyclopropyl,i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. The term“cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety.The term “cycloalkylalkenyl” denotes cycloalkyl substitution on analkenyl moiety. The term “cycloalkylalkynyl” denotes cycloalkylsubstitution on an alkynyl moiety. Examples of “cycloalkylalkyl” includecyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moietiesbonded to straight-chain or branched alkyl groups. The term“cycloalkoxy” denotes cycloalkyl linked through an oxygen atom such ascyclopentyloxy and cyclohexyloxy. “Cycloalkylalkoxy” denotescycloalkylalkyl linked through an oxygen atom attached to the alkylchain. Examples of “cycloalkylalkoxy” include cyclopropylmethoxy,cyclopentylethoxy, and other cycloalkyl moieties bonded tostraight-chain or branched alkoxy groups. “Cycloalkenyl” includes groupssuch as cyclopentenyl and cyclohexenyl as well as groups with more thanone double bond such as 1,3- and 1,4-cyclohexadienyl. The term“cycloalkylcycloalkyl” means a cycloalkyl substitution on a cycloalkylmoiety”. The terms “cycloalkoxyalkyl”, “alkylcycloalkyl”,“cycloalkylaminoalkyl”, “cycloalkylthio”, “cycloalkylsulfinyl”,“cycloalkylsulfonyl” and the like are defined likewise.

The term “halogen”, either alone or in compound words such as“haloalkyl”, or when used in descriptions such as “alkyl substitutedwith halogen” includes fluorine, chlorine, bromine or iodine. Further,when used in compound words such as “haloalkyl”, or when used indescriptions such as “alkyl substituted with halogen” said alkyl may bepartially or fully substituted with halogen atoms which may be the sameor different. Examples of “haloalkyl” or “alkyl substituted withhalogen” include F₃C, ClCH₂, CF₃CH₂ and CF₃CCl₂. The terms“halocycloalkyl”, “haloalkoxy”, “haloalkylthio”, “haloalkenyl”,“haloalkynyl”, and the like, are is defined analogously to the term“haloalkyl”. Examples of “haloalkoxy” include CF₃O—, CCl₃CH₂O—,HCF₂CH₂CH₂O— and CF₃CH₂O—. Examples of “haloalkylthio” include CCl₃S—,CF₃S—, CCl₃CH₂S— and ClCH₂CH₂CH₂S—. Examples of “haloalkylsulfinyl”include CF₃S(O)—, CCl₃S(O)—, CF₃CH₂S(O)— and CF₃CF₂S(O)—. Examples of“haloalkylsulfonyl” include CF₃S(O)₂—, CCl₃S(O)₂—, CF₃CH₂S(O)₂— andCF₃CF₂S(O)₂—. Examples of “haloalkenyl” include (Cl)₂C═CHCH₂— andCF₃CH₂CH═CHCH₂—. Examples of “haloalkynyl” include HC≡CCHCl—, CF₃C≡C—,CCl₃C≡C— and FCH₂C≡CCH₂—. Examples of “haloalkoxyalkoxy” includeCF₃OCH₂O—, ClCH₂CH₂OCH₂CH₂O—, Cl₃CCH₂OCH₂O— as well as branched alkylderivatives. Examples of the “haloalkenyloxy” include (Cl)₂C═CHCH₂O— andCF₃CH₂CH═CHCH₂O—. Examples of “haloalkoxyalkyl” include CF₃OCH₂—,CCl₃CH₂OCH₂—, HCF₂CH₂CH₂OCH₂- and CF₃CH₂OCH₂—.

“Alkylcarbonyl” denotes a straight-chain or branched alkyl moietiesbonded to a C(═O) moiety. Examples of “alkylcarbonyl” include CH₃C(═O)—,CH₃CH₂CH₂C(═O)— and (CH₃)₂CHC(═O)—. Examples of“alkoxycarbonyl” includeCH₃OC(═O)—, CH₃CH₂OC(═O)—, CH₃CH₂CH₂OC(═O)—, (CH₃)₂CHOC(═O)— and thedifferent butoxy- or pentoxycarbonyl isomers. The terms“alkylcarbonylalkyl”, “alkylcarbonyloxy”, “alkoxycarbonylamino”,“alkylaminocarbonyl”, “dialkylaminosulfonyl” “cycloalkylcarbonyl”,“cycloalkoxycarbonyl”, “cycloalkylcarbonyloxy”, “dialkylaminocarbonyl”“cycloalkylaminocarbonyl”, “haloalkylcarbonyl” and “haloalkoxycarbonyl”are defined likewise. The terms “cyanoalkyl” refers to a cyano groupattached to an alkyl group. The terms “cyanoalkoxy” refers to a cyanogroup attached to an alkoxy group. The terms “nitroalkyl” refers to anitro group attached to an alkyl group. The terms “nitroalkenyl” refersto a nitro group attached to an alkenyl group.

The term “trialkylsilyl” means silyl substituted with three alkylgroups. The term “trialkylsilylalkyl” means refers to a trialkylsilylgroup bonded through an alkyl group (e.g. —CH₂TMS). The term“trialkylsilyloxy” means refers to a trialkylsilyl group bonded throughoxygen (e.g. -OTMS).

The total number of carbon atoms in a substituent group is indicated bythe “C_(i)-C_(j)” prefix where i and j are numbers from 1 to 12. Forexample, C₁-C₄ alkylsulfonyl designates methylsulfonyl throughbutylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂—; C₃ alkoxyalkyldesignates, for example, CH₃CH(OCH₃)—, CH₃OCH₂CH₂— or CH₃CH₂OCH₂—; andC₄ alkoxyalkyl designates the various isomers of an alkyl groupsubstituted with an alkoxy group containing a total of four carbonatoms, examples including CH₃CH₂CH₂OCH₂— and CH₃CH₂OCH₂CH₂—.

When a compound is substituted with a substituent bearing a subscriptthat indicates the number of said substituents can exceed 1, saidsubstituents (when they exceed 1) are independently selected from thegroup of defined substituents, e.g., (R⁷)_(n), n is 1, 2, 3, 4 or 5.Further, when the subscript indicates a range, e.g. (R)_(i-j), then thenumber of substituents may be selected from the integers between i and jinclusive. When a group contains a substituent which can be hydrogen,for example R¹ or R², then when this substituent is taken as hydrogen,it is recognized that this is equivalent to said group beingunsubstituted. When a variable group is shown to be optionally attachedto a position, for example (R⁷)_(n) wherein n may be 0, then hydrogenmay be at the position even if not recited in the variable groupdefinition. When one or more positions on a group are said to be “notsubstituted” or “unsubstituted”, then hydrogen atoms are attached totake up any free valency.

Unless otherwise indicated, a “ring” or “ring system” as a component ofFormula 1 (e.g., substituent Q¹) is carbocyclic or heterocyclic. Theterm “ring system” denotes two or more fused rings. The terms “bicyclicring system” and “fused bicyclic ring system” denote a ring systemconsisting of two fused rings, in which either ring can be saturated,partially unsaturated, or fully unsaturated unless otherwise indicated.The term “fused heterobicyclic ring system” denotes a fused bicyclicring system in which at least one ring atom is not carbon. A “bridgedbicyclic ring system” is formed by bonding a segment of one or moreatoms to nonadjacent ring members of a ring. The term “ring member”refers to an atom or other moiety (e.g., C(═O), C(═S), S(O) or S(O)₂)forming the backbone of a ring or ring system.

The terms “heterocyclic ring”, “heterocycle” or “heterocyclic ringsystem” denote a ring or ring system in which at least one atom formingthe ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur.Typically a heterocyclic ring contains no more than 4 nitrogens, no morethan 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, aheterocyclic ring can be a saturated, partially unsaturated, or fullyunsaturated ring. When a fully unsaturated heterocyclic ring satisfiesHickel's rule, then said ring is also called a “heteroaromatic ring” or“aromatic heterocyclic ring”. Unless otherwise indicated, heterocyclicrings and ring systems can be attached through any available carbon ornitrogen by replacement of a hydrogen on said carbon or nitrogen.

“Aromatic” indicates that each of the ring atoms is essentially in thesame plane and has a p-orbital perpendicular to the ring plane, and that(4n+2) πelectrons, where n is a positive integer, are associated withthe ring to comply with Hickel's rule. The term “aromatic ring system”denotes a carbocyclic or heterocyclic ring system in which at least onering of the ring system is aromatic. The term “aromatic carbocyclic ringsystem” denotes a carbocyclic ring system in which at least one ring ofthe ring system is aromatic. The term “aromatic heterocyclic ringsystem” denotes a heterocyclic ring system in which at least one ring ofthe ring system is aromatic. The term “nonaromatic ring system” denotesa carbocyclic or heterocyclic ring system that may be fully saturated,as well as partially or fully unsaturated, provided that none of therings in the ring system are aromatic. The term “nonaromatic carbocyclicring system” in which no ring in the ring system is aromatic. The term“nonaromatic heterocyclic ring system” denotes a heterocyclic ringsystem in which no ring in the ring system is aromatic.

The term “optionally substituted” in connection with the heterocyclicrings refers to groups which are unsubstituted or have at least onenon-hydrogen substituent that does not extinguish the biologicalactivity possessed by the unsubstituted analog. As used herein, thefollowing definitions shall apply unless otherwise indicated. The term“optionally substituted” is used interchangeably with the phrase“substituted or unsubstituted” or with the term “(un)substituted.”Unless otherwise indicated, an optionally substituted group may have asubstituent at each substitutable position of the group, and eachsubstitution is independent of the other.

When Q¹ or Q² is a 5- or 6-membered nitrogen-containing heterocyclicring, it may be attached to the remainder of Formula 1 though anyavailable carbon or nitrogen ring atom, unless otherwise described. Asnoted above, Q¹ and Q² can be (among others) phenyl optionallysubstituted with one or more substituents selected from a group ofsubstituents as defined in the Summary of the Invention. An example ofphenyl optionally substituted with one to five substituents is the ringillustrated as U-1 in Exhibit 1, wherein R^(v) is R⁷ as defined in theSummary of the Invention for Q¹, or R^(v) is R¹⁰ as defined in theSummary of the Invention for Q², and r is an integer from 0 to 5.

As noted above, Q¹ and Q² can be (among others) a 5- or 6-memberedheterocyclic ring, which may be saturated or unsaturated, optionallysubstituted with one or more substituents selected from a group ofsubstituents as defined in the Summary of the Invention. Examples of a5- or 6-membered unsaturated aromatic heterocyclic ring optionallysubstituted with from one or more substituents include the rings U-2through U-61 illustrated in Exhibit 1 wherein R^(v) is any substituentas defined in the Summary of the Invention for Q¹ and Q² (e.g. R⁷ for Q¹or R¹⁰ for Q²) and r is an integer from 0 to 4, limited by the number ofavailable positions on each U group. As U-29, U-30, U-36, U-37, U-38,U-39, U-40, U-41, U-42 and U-43 have only one available position, forthese U groups r is limited to the integers 0 or 1, and r being 0 meansthat the U group is unsubstituted and a hydrogen is present at theposition indicated by (R^(v))_(r).

Exhibit 1

As noted above, Q¹ and Q² can be (among others) an 8-, 9- or 10-memberedfused bicyclic ring system optionally substituted with one or moresubstituents selected from a group of substituents as defined in theSummary of the Invention (e.g. R⁷ for Q¹ or R¹⁰ for Q²). Examples of an8-, 9- or 10-membered fused bicyclic ring system optionally substitutedwith from one or more substituents include the rings U-81 through U-123illustrated in Exhibit 2 wherein R^(v) is any substituent as defined inthe Summary of the Invention for Q¹ or Q² (e.g. R⁷ for Q¹ or R¹⁰ forQ²), and r is typically an integer from 0 to 5.

Exhibit 2

Although R^(v) groups are shown in the structures U-1 through U-100, itis noted that they do not need to be present since they are optionalsubstituents. Note that when R^(v) is H when attached to an atom, thisis the same as if said atom is unsubstituted. The nitrogen atoms thatrequire substitution to fill their valence are substituted with H orR^(v). Note that when the attachment point between (R^(v))_(r) and the Ugroup is illustrated as floating, (R^(v))_(r) can be attached to anyavailable carbon atom or nitrogen atom of the U group. Note that whenthe attachment point on the U group is illustrated as floating, the Ugroup can be attached to the remainder of Formula 1 through anyavailable carbon or nitrogen of the U group by replacement of a hydrogenatom. Note that some U groups can only be substituted with less than 4R^(v) groups (e.g., U-2 through U-5, U-7 through U-48, and U-52 throughU-61).

A wide variety of synthetic methods are known in the art to enablepreparation of aromatic and nonaromatic heterocyclic rings and ringsystems; for extensive reviews see the eight volume set of ComprehensiveHeterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief,Pergamon Press, Oxford, 1984 and the twelve volume set of ComprehensiveHeterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V.Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersand geometric isomers. Stereoisomers are isomers of identicalconstitution but differing in the arrangement of their atoms in spaceand include enantiomers, diastereomers, cis-trans isomers (also known asgeometric isomers) and atropisomers. Atropisomers result from restrictedrotation about single bonds where the rotational barrier is high enoughto permit isolation of the isomeric species. One skilled in the art willappreciate that one stereoisomer may be more active and/or may exhibitbeneficial effects when enriched relative to the other stereoisomer(s)or when separated from the other stereoisomer(s). Additionally, theskilled artisan knows how to separate, enrich, and/or to selectivelyprepare said stereoisomers. The compounds of the invention may bepresent as a mixture of stereoisomers, individual stereoisomers or as anoptically active form. Particularly when R⁴ and R⁵ are each H, theC(Y²)N(Q²)(R¹) and Q¹ substituents are typically mostly in thethermodynamically preferred trans configuration on the butyrolactonering.

For example the C(O)N(Q²)(R¹) moiety (bonded to the carbon at the3-position of the butyrolactone ring) and Q¹ (bonded to the carbon atthe 4-position of the pyrrolidinone ring) are generally found in thetrans configuration. These two carbon atoms (i.e. at the 3- and4-positions of the butyrolactone ring of Formula 1) both possess achiral center. The two most prevelant pairs of enantiomers are depictedas Formula 1′ and Formula 1″ where the chiral centers are identified(i.e. as 3S,4R or as 3R,4S). While this invention pertains to allstereoisomers, the preferred enantiomeric pair for biologicaloperability is identified as Formula 1′ (i.e. the 3S,4R configuration).The skilled artisan will understand that in some Embodiments of theinvention, the R or S designation is determined relative to othersubstituents around the same carbon and therefore a compound of theinvention could also be given the 3S,4S designation. For a comprehensivediscussion of all aspects of stereoisomerism, see Ernest L. Eliel andSamuel H. Wilen, Stereochemistry of Organic Compounds, John Wiley &Sons, 1994.

The skilled artisan will also recognize that the carbon atom at the5-position of the butyrolactone ring (i.e. the carbon atom to which bothR² and R³ are bonded) also contains a stereocenter indicated by a (*) asshown in Formula 1′″ when R² and R³ are other than the same substituent.This invention pertains to all stereoisomers, and therefore, when R² andR³ are other than the same substituent, then a mixture of diastereomersis possible.

Molecular depictions drawn herein follow standard conventions fordepicting stereochemistry. To indicate stereoconfiguration, bonds risingfrom the plane of the drawing and towards the viewer are denoted bysolid wedges wherein the broad end of the wedge is attached to the atomrising from the plane of the drawing towards the viewer. Bonds goingbelow the plane of the drawing and away from the viewer are denoted bydashed wedges wherein the narrow end of the wedge is attached to theatom further away from the viewer. Constant width lines indicate bondswith a direction opposite or neutral relative to bonds shown with solidor dashed wedges; constant width lines also depict bonds in molecules orparts of molecules in which no particular stereoconfiguration isintended to be specified.

This invention comprises racemic mixtures, for example, equal amounts ofthe enantiomers of Formulae 1′ and 1″. In addition, this inventionincludes compounds that are enriched compared to the racemic mixture inan enantiomer of Formula 1. Also included are the essentially pureenantiomers of compounds of Formula 1, for example, Formula 1′ andFormula 1″.

When enantiomerically enriched, one enantiomer is present in greateramounts than the other, and the extent of enrichment can be defined byan expression of enantiomeric excess (“ee”), which is defined as (2×−1)100%, where x is the mole fraction of the dominant enantiomer in themixture (e.g., an ee of 20% corresponds to a 60:40 ratio ofenantiomers).

Preferably the compositions of this invention have at least a 50%enantiomeric excess; more preferably at least a 75% enantiomeric excess;still more preferably at least a 90% enantiomeric excess; and the mostpreferably at least a 94% enantiomeric excess of the more active isomer.Of particular note are enantiomerically pure embodiments of the moreactive isomer.

Compounds of Formula 1 can comprise additional chiral centers. Forexample, substituents and other molecular constituents such as R² and R³may themselves contain chiral centers. This invention comprises racemicmixtures as well as enriched and essentially pure stereoconfigurationsat these additional chiral centers.

Compounds of this invention can exist as one or more conformationalisomers due to restricted rotation about the amide bond C(Y²)N(Q²)(R¹)in Formula 1. This invention comprises mixtures of conformationalisomers. In addition, this invention includes compounds that areenriched in one conformer relative to others.

Compounds of Formula 1 typically exist in more than one form, andFormula 1 thus includes all crystalline and non-crystalline forms of thecompounds they represent. Non-crystalline forms include embodimentswhich are solids such as waxes and gums as well as embodiments which areliquids such as solutions and melts. Crystalline forms includeembodiments which represent essentially a single crystal type andembodiments which represent a mixture of polymorphs (i.e. differentcrystalline types). The term “polymorph” refers to a particularcrystalline form of a chemical compound that can crystallize indifferent crystalline forms, these forms having different arrangementsand/or conformations of the molecules in the crystal lattice. Althoughpolymorphs can have the same chemical composition, they can also differin composition due the presence or absence of co-crystallized water orother molecules, which can be weakly or strongly bound in the lattice.Polymorphs can differ in such chemical, physical and biologicalproperties as crystal shape, density, hardness, color, chemicalstability, melting point, hygroscopicity, suspensibility, dissolutionrate and biological availability. One skilled in the art will appreciatethat a polymorph of a compound of Formula 1 can exhibit beneficialeffects (e.g., suitability for preparation of useful formulations,improved biological performance) relative to another polymorph or amixture of polymorphs of the same compound of Formula 1. Preparation andisolation of a particular polymorph of a compound of Formula 1 can beachieved by methods known to those skilled in the art including, forexample, crystallization using selected solvents and temperatures. For acomprehensive discussion of polymorphism see R. Hilfiker, Ed.,Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.

One skilled in the art will appreciate that not all nitrogen-containingheterocycles can form N-oxides since the nitrogen requires an availablelone pair for oxidation to the oxide; one skilled in the art willrecognize those nitrogen-containing heterocycles which can formN-oxides. One skilled in the art will also recognize that tertiaryamines can form N-oxides. Synthetic methods for the preparation ofN-oxides of heterocycles and tertiary amines are very well known by oneskilled in the art including the oxidation of heterocycles and tertiaryamines with peroxy acids such as peracetic and m-chloroperbenzoic acid(MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butylhydroperoxide, sodium perborate, and dioxiranes such asdimethyldioxirane. These methods for the preparation of N-oxides havebeen extensively described and reviewed in the literature, see forexample: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik inComprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boultonand A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keenein Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R.Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advancesin Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J.Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G.Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A.R. Katritzky and A. J. Boulton, Eds., Academic Press.

One skilled in the art recognizes that because in the environment andunder physiological conditions salts of chemical compounds are inequilibrium with their corresponding nonsalt forms, salts share thebiological utility of the nonsalt forms. Thus a wide variety of salts ofa compound of Formula 1 are useful for control of undesired vegetation(i.e. are agriculturally suitable). The salts of a compound of Formula 1include acid-addition salts with inorganic or organic acids such ashydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic,butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic,tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula1 contains an acidic moiety such as a carboxylic acid or phenol, saltsalso include those formed with organic or inorganic bases such aspyridine, triethylamine or ammonia, or amides, hydrides, hydroxides orcarbonates of sodium, potassium, lithium, calcium, magnesium or barium.Accordingly, the present invention comprises compounds selected fromFormula 1, N-oxides and agriculturally suitable salts thereof.

Embodiments of the present invention as described in the Summary of theInvention include (where Formula 1 as used in the following Embodimentsincludes N-oxides and salts thereof):

Embodiment 1

A compound of Formula 1 (including all stereoisomers), N-oxides, andsalts thereof, agricultural compositions containing them and their useas herbicides as described in the Summary of the Invention.

Embodiment 2

A compound of Formula 1 wherein when Q¹ is an 8- to 10-memberedheteroaromatic bicyclic ring system optionally substituted with R⁷ andR⁹, the remainder of Formula 1 is bonded to a fully unsaturated ring ofsaid bicyclic ring system.

Embodiment 3

A compound of Formula 1 wherein Q¹ is a phenyl ring optionallysubstituted with up to 5 substituents independently selected from R⁷.

Embodiment 4

A compound of Embodiment 3 wherein Q¹ is a phenyl ring substituted with1 to 3 substituents independently selected from R⁷.

Embodiment 5

A compound of Embodiment 4 wherein Q¹ is a phenyl ring substituted with1 to 2 substituents independently selected from R⁷.

Embodiment 6

A compound of Formula 1 or any one of Embodiments 3 through 5 wherein Q¹is a phenyl ring having a substituent selected from R⁷ at the para (4-)position (and optionally other substituents).

Embodiment 7

A compound of Formula 1 or any one of Embodiments 3 through 6 whereinwhen Q¹ is a phenyl ring substituted with at least two substituentsselected from R⁷, then one substituent is at the para (4-) position andat least one other substituent is at a meta position (of the phenylring).

Embodiment 8

A compound of Formula 1 or any one of Embodiments 2 through 7 whereinwhen Q² is an 8- to 10-membered heteroaromatic bicyclic ring systemoptionally substituted with R¹⁰ and R¹¹, the remainder of Formula 1 isbonded to a fully unsaturated ring of said bicyclic ring system.

Embodiment 9

A compound of Formula 1 or any one of Embodiments 2 through 7 wherein Q²is a phenyl ring substituted with up to 5 substituents independentlyselected from R¹⁰.

Embodiment 10

A compound of Embodiment 9 wherein Q² is a phenyl ring substituted with1 to 3 substituents independently selected from R¹⁰.

Embodiment 11

A compound of Embodiment 10 wherein Q² is a phenyl ring substituted with1 to 2 substituents independently selected from R¹⁰.

Embodiment 12

A compound of Embodiment 11 wherein Q² is a phenyl ring having at leastone substituent selected from R¹⁰ at an ortho (e.g., 2-) position (andoptionally other substituents).

Embodiment 13

A compound of Formula 1 or any one of Embodiments 2 through 7 orEmbodiments 9 through 12 wherein when Q² is a phenyl ring substitutedwith at least two substituents selected from R¹⁰, then at least onesubstituent is at an ortho (e.g., 2-) position and at least onesubstituent is at an adjacent meta (e.g., 3-) position (of the phenylring).

Embodiment 14

A compound of Formula 1 or any one of Embodiments 2 through 13 wherein,independently, each R⁷ and R¹⁰ is independently halogen, cyano, nitro,C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl C₂-C₄alkynyl, C₂-C₄ haloalkynyl, C₁-C₄ nitroalkyl, C₂-C₄ nitroalkenyl, C₂-C₄alkoxyalkyl, C₂-C₄ haloalkoxyalkyl, C₃-C₄ cycloalkyl, C₃-C₄halocycloalkyl, cyclopropylmethyl, methylcyclopropyl, C₁-C₄ alkoxy,C₁-C₄ haloalkoxy, C₂-C₄ alkenyloxy, C₂-C₄ haloalkenyloxy, C₃-C₄alkynyloxy, C₃-C₄ haloalkynyloxy, C₃-C₄ cycloalkoxy, C₁-C₄ alkylthio,C₁-C₄ haloalkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ haloalkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄ haloalkylsulfonyl, hydroxy, formyl, C₂-C₄alkylcarbonyl, C₂-C₄ alkylcarbonyloxy, C₁-C₄ alkylsulfonyloxy, C₁-C₄haloalkylsulfonyloxy, amino, C₁-C₄ alkylamino, C₂-C₄ dialkylamino,formylamino, C₂-C₄ alkylcarbonylamino, —SF₅, —SCN, C₃-C₄ trialkylsilyl,trimethylsilylmethyl or trimethylsilylmethoxy.

Embodiment 15

A compound of Embodiment 14 wherein each R⁷ is independently halogen,cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenylC₂-C₄ alkynyl, C₂-C₄ haloalkynyl, C₃-C₄ cycloalkyl, C₃-C₄halocycloalkyl, cyclopropylmethyl, methylcyclopropyl, C₁-C₄ alkoxy,C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, C₁-C₄alkylsulfonyl, C₁-C₄ alkylsulfonyloxy or C₁-C₄ haloalkylsulfonyloxy.

Embodiment 16

A compound of Embodiment 15 wherein each R⁷ is independently halogen,cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl C₁-C₄ alkoxy or C₁-C₄ haloalkoxy.

Embodiment 17

A compound of Embodiment 16 wherein each R⁷ is independently halogen,C₁-C₂ alkyl or C₁-C₃ haloalkyl.

Embodiment 18

A compound of Embodiment 17 wherein each R⁷ is independently halogen orC₁-C₂ haloalkyl.

Embodiment 19

A compound of Embodiment 18 wherein each R⁷ is independently halogen orC₁ haloalkyl.

Embodiment 20

A compound of Embodiment 19 wherein each R⁷ is independently halogen orC₁ fluoroalkyl.

Embodiment 21

A compound of Embodiment 20 wherein each R⁷ is independently halogen orCF₃.

Embodiment 22

A compound of Embodiment 21 wherein each R⁷ is independently F, Cl, Bror CF₃.

Embodiment 23

A compound of Embodiment 22 wherein each R⁷ is independently F or CF₃.

Embodiment 24

A compound of any one of Embodiments 21 through 23 wherein at most onlyone CF₃ substituent is present on the Q¹ phenyl ring and is at the metaposition of said phenyl ring.

Embodiment 25

A compound any one of Embodiments 14 through 24 wherein each R¹⁰ isindependently halogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄alkenyl, C₂-C₄ haloalkenyl C₂-C₄ alkynyl, C₂-C₄ haloalkynyl, C₃-C₄cycloalkyl, C₃-C₄ halocycloalkyl, cyclopropylmethyl, methylcyclopropyl,C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio,C₁-C₄ alkylsulfonyl, C₁-C₄ alkylsulfonyloxy or C₁-C₄haloalkylsulfonyloxy.

Embodiment 26

A compound of Embodiment 25 wherein each R¹⁰ is independently halogen,cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl or C₁-C₄ alkylsulfonyl.

Embodiment 27

A compound of Embodiment 26 wherein each R¹⁰ is independently halogen,cyano, C₁-C₂ alkyl, C₁-C₃ haloalkyl or C₁-C₃ alkylsulfonyl.

Embodiment 28

A compound of Embodiment 27 wherein each R¹⁰ is independently halogen,C₁-C₂ haloalkyl or C₁-C₃ alkylsulfonyl.

Embodiment 29

A compound of Embodiment 28 wherein each R¹⁰ is independently halogen,C₁ haloalkyl or C₁ alkylsulfonyl.

Embodiment 30

A compound of Embodiment 29 wherein each R¹⁰ is independently halogen orC₁ fluoroalkyl.

Embodiment 31

A compound of Embodiment 30 wherein each R¹⁰ is independently halogen orCF₃.

Embodiment 32

A compound of Embodiment 31 wherein each R¹⁰ is independently F, Cl, Bror CF₃.

Embodiment 33

A compound of Embodiment 32 wherein each R¹⁰ is independently F or CF₃.

Embodiment 34

A compound of Embodiment 33 wherein each R¹⁰ is F.

Embodiment 35

A compound of Formula 1 or any one of Embodiments 2 through 34 wherein,independently, each R⁹ and R¹¹ is independently C₁-C₂ alkyl or C₂-C₃alkoxycarbonyl.

Embodiment 36

A compound of Embodiment 35 wherein, independently, each R⁹ and R¹¹ isindependently C₁-C₂ alkyl.

Embodiment 37

A compound of Embodiment 36 wherein, independently, each R⁹ and R¹¹ isCH₃.

Embodiment 38

A compound of Formula 1 or any one of Embodiments 2 through 37 whereinY¹ is O.

Embodiment 39

A compound of Formula 1 or any one of Embodiments 2 through 38 whereinY² is O.

Embodiment 40

A compound of Formula 1 or any one of Embodiments 2 through 39 whereinR² is H or CH₃.

Embodiment 41

A compound of Embodiment 40 wherein R² is H.

Embodiment 42

A compound of Formula 1 or any one of Embodiments 2 through 41 whereinR³ is H or CH₃.

Embodiment 43

A compound of Embodiment 42 wherein R³ is H.

Embodiment 44

A compound of Formula 1 or any one of Embodiments 2 through 44 whereinR⁴ is H or CH₃.

Embodiment 45

A compound of Embodiment 44 wherein R⁴ is H.

Embodiment 46

A compound of Formula 1 or any one of Embodiments 2 through 45 whereinR⁵ is H or CH₃.

Embodiment 47

A compound of Embodiment 46 wherein R⁵ is H.

Embodiment 48

A compound of Formula 1 or any one of Embodiments 2 through 47 whereinR¹ is H, hydroxy, amino, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl,C₃-C₄ alkynyl, C₂-C₄ alkoxyalkyl, C₂-C₄ haloalkoxyalkyl, C₂-C₄alkylthioalkyl, C₂-C₄ alkylsulfinylalkyl, C₂-C₄ alkylsulfonylalkyl,C₂-C₄ alkylcarbonyl, C₂-C₄ haloalkylcarbonyl, C₄-C₆ cycloalkylcarbonyl,C₂-C₄ alkoxycarbonyl, C₂-C₄ haloalkoxycarbonyl or C₄-C₆cycloalkoxycarbonyl.

Embodiment 49

A compound of Embodiment 48 wherein R¹ is H, hydroxy, amino, C₁-C₃alkyl, C₁-C₃ haloalkyl, C₂-C₄ alkenyl or C₃-C₄ alkynyl.

Embodiment 50

A compound of Embodiment 49 wherein R¹ is H or C₁-C₃ alkyl.

Embodiment 51

A compound of Embodiment 50 wherein R¹ is H or CH₃.

Embodiment 52

A compound of Embodiment 51 wherein R¹ is H.

Embodiment 53

A compound of Formula 1 or any one of Embodiments 2 through 52 whereinthe stereochemistry is (3R,4S) or (3S,4R).

Embodiment 54

A compound of Embodiment 53 wherein the stereochemistry is (3R,4S).

Embodiment 55

A compound of Embodiment 53 wherein the stereochemistry is (3S,4R).

Embodiment 56

A compound of Formula 1 or any one of Embodiments 2 through 46 whereinR⁵ is CH₃.

Embodiment 57

A compound Formula 1 wherein Q¹ is a phenyl ring optionally substitutedwith 1 to 4 substituents independently selected from R⁷; or a 5- to6-membered heteroaromatic ring containing ring members selected fromcarbon atoms and 1 to 4 heteroatoms independently selected from up to 2O, up to 2 S and up to 4 N atoms, optionally substituted with up to 4substituents independently selected from R⁷ on carbon atom ring membersand selected from R⁹ on nitrogen atom ring members.

Embodiment 58

A compound of Formula 1 wherein Q² is a phenyl ring optionallysubstituted with up to 5 substituents independently selected from R¹⁰;or a 5- to 6-membered heteroaromatic ring containing ring membersselected from carbon atoms and 1 to 4 heteroatoms independently selectedfrom up to 2 O, up to 2 S and up to 4 N atoms, optionally substitutedwith up to 5 substituents independently selected from R¹⁰ on carbon atomring members and selected from R¹¹ on nitrogen atom ring members.

Embodiment 59

A compound of Formula 1 wherein Q¹ is a 5- to 6-membered heteroaromaticring or an 8- to 10-membered heteroaromatic bicyclic ring system, eachring or ring system optionally substituted with up to 4 substituentsindependently selected from R⁷ on carbon atom ring members and selectedfrom R⁹ on nitrogen atom ring members.

Embodiments of this invention, including Embodiments 1-59 above as wellas any other embodiments described herein, can be combined in anymanner, and the descriptions of variables in the embodiments pertain notonly to the compounds of Formula 1 but also to the starting compoundsand intermediate compounds useful for preparing the compounds ofFormula 1. In addition, embodiments of this invention, includingEmbodiments 1-59 above as well as any other embodiments describedherein, and any combination thereof, pertain to the compositions andmethods of the present invention.

Combinations of Embodiments 1-59 are illustrated by:

Embodiment A

A compound of Formula 1 wherein

-   -   each R⁷ and R¹⁰ is independently halogen, cyano, nitro, C₁-C₄        alkyl, C₁-C₄ haloalkyl, C₂-C₄ alkenyl, C₂-C₄ haloalkenyl C₂-C₄        alkynyl, C₂-C₄ haloalkynyl, C₁-C₄ nitroalkyl, C₂-C₄        nitroalkenyl, C₂-C₄ alkoxyalkyl, C₂-C₄ haloalkoxyalkyl, C₃-C₄        cycloalkyl, C₃-C₄ halocycloalkyl, cyclopropylmethyl,        methylcyclopropyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₂-C₄        alkenyloxy, C₂-C₄ haloalkenyloxy, C₃-C₄ alkynyloxy, C₃-C₄        haloalkynyloxy, C₃-C₄ cycloalkoxy, C₁-C₄ alkylthio, C₁-C₄        haloalkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ haloalkylsulfinyl,        C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylsulfonyl, hydroxy, formyl,        C₂-C₄ alkylcarbonyl, C₂-C₄ alkylcarbonyloxy, C₁-C₄        alkylsulfonyloxy, C₁-C₄ haloalkylsulfonyloxy, amino, C₁-C₄        alkylamino, C₂-C₄ dialkylamino, formylamino, C₂-C₄        alkylcarbonylamino, —SF₅, —SCN, C₃-C₄ trialkylsilyl,        trimethylsilylmethyl or trimethylsilylmethoxy; and    -   each R⁹ and R¹¹ is independently C₁-C₂ alkyl or C₂-C₃        alkoxycarbonyl.

Embodiment B

A compound of Embodiment A wherein

-   -   Y¹ is O;    -   Y² is O;    -   R¹ is H;    -   R² is H;    -   R³ is H;    -   R⁴ is H; and    -   R⁵ is H.

Embodiment C

A compound of Embodiment B wherein

-   -   Q¹ is a phenyl ring substituted with 1 to 3 substituents        independently selected from R⁷; and    -   Q² is a phenyl ring substituted with 1 to 3 substituents        independently selected from R¹⁰.

Embodiment D

A compound of Embodiment C wherein

-   -   each R⁷ is independently halogen, cyano, C₁-C₄ alkyl, C₁-C₄        haloalkyl C₁-C₄ alkoxy or C₁-C₄ haloalkoxy; and    -   each R¹⁰ is independently halogen, cyano, C₁-C₄ alkyl, C₁-C₄        haloalkyl or C₁-C₄ alkylsulfonyl.

Embodiment E

A compound of Embodiment D wherein

-   -   Q¹ is a phenyl ring substituted with 1 substituent selected from        R⁷ at the para position or substituted with 2 substituents        independently selected from R⁷ wherein one substituent is at the        para position and the other substituent is at a meta position;        and    -   Q² is a phenyl ring substituted with 1 substituent selected from        R¹⁰ at an ortho position or substituted with 2 substituents        independently selected from R¹⁰ wherein one substituent is at an        ortho position and the other substituent is at the adjacent meta        position.

Embodiment F

A compound of Embodiment E wherein

-   -   each R⁷ is independently F or CF₃; and    -   each R¹⁰ is F.

Embodiment G

A compound of Embodiment A wherein

-   -   Y¹ is O;    -   Y² is O;    -   R¹ is H;    -   R² is H;    -   R³ is H;    -   R⁴ is H; and    -   R⁵ is H or CH₃.

Specific embodiments include a compound of Formula 1 selected from thegroup consisting of:

-   4-(4-fluorophenyl)tetrahydro-2-oxo-N-[2-(trifluoromethyl)phenyl)]-3-furancarboxamide;-   (3R,4S)-4-(4-fluorophenyl)tetrahydro-2-oxo-N-[2-(trifluoromethyl)phenyl)]-3-furancarboxamide;    and-   (3S,4R)-4-(4-fluorophenyl)tetrahydro-2-oxo-N-[2-(trifluoromethyl)phenyl)]-3-furancarboxamide.

This invention also relates to a method for controlling undesiredvegetation comprising applying to the locus of the vegetationherbicidally effective amounts of the compounds of the invention (e.g.,as a composition described herein). Of note as embodiments relating tomethods of use are those involving the compounds of embodimentsdescribed above. Compounds of the invention are particularly useful forselective control of weeds in crops such as wheat, barley, maize,soybean, sunflower, cotton, oilseed rape and rice, and specialty cropssuch as sugarcane, citrus, fruit and nut crops.

Also noteworthy as embodiments are herbicidal compositions of thepresent invention comprising the compounds of embodiments describedabove.

This invention also includes a herbicidal mixture comprising (a) acompound selected from Formula 1, N-oxides, and salts thereof, and (b)at least one additional active ingredient selected from (b1) photosystemII inhibitors, (b2) acetohydroxy acid synthase (AHAS) inhibitors, (b3)acetyl-CoA carboxylase (ACCase) inhibitors, (b4) auxin mimics, (b5)5-enol-pyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (b6)photosystem I electron diverters, (b7) protoporphyrinogen oxidase (PPO)inhibitors, (b8) glutamine synthetase (GS) inhibitors, (b9) very longchain fatty acid (VLCFA) elongase inhibitors, (b10) auxin transportinhibitors, (b11) phytoene desaturase (PDS) inhibitors, (b12)4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, (b13)homogentisate solenesyltransererase (HST) inhibitors, (b14) cellulosebiosynthesis inhibitors, (b15) other herbicides including mitoticdisruptors, organic arsenicals, asulam, bromobutide, cinmethylin,cumyluron, dazomet, difenzoquat, dymron, etobenzanid, flurenol,fosamine, fosamine-ammonium, hydantocidin, metam, methyldymron, oleicacid, oxaziclomefone, pelargonic acid and pyributicarb, and (b16)herbicide safeners; and salts of compounds of (b1) through (b16).

“Photosystem II inhibitors” (b1) are chemical compounds that bind to theD-1 protein at the Q_(B)-binding niche and thus block electron transportfrom Q_(A) to Q_(B) in the chloroplast thylakoid membranes. Theelectrons blocked from passing through photosystem II are transferredthrough a series of reactions to form toxic compounds that disrupt cellmembranes and cause chloroplast swelling, membrane leakage, andultimately cellular destruction. The Q_(B)-binding niche has threedifferent binding sites: binding site A binds the triazines such asatrazine, triazinones such as hexazinone, and uracils such as bromacil,binding site B binds the phenylureas such as diuron, and binding site Cbinds benzothiadiazoles such as bentazon, nitriles such as bromoxyniland phenyl-pyridazines such as pyridate. Examples of photosystem IIinhibitors include ametryn, amicarbazone, atrazine, bentazon, bromacil,bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron,chloroxuron, cumyluron, cyanazine, daimuron, desmedipham, desmetryn,dimefuron, dimethametryn, diuron, ethidimuron, fenuron, fluometuron,hexazinone, ioxynil, isoproturon, isouron, lenacil, linuron, metamitron,methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron,neburon, pentanochlor, phenmedipham, prometon, prometryn, propanil,propazine, pyridafol, pyridate, siduron, simazine, simetryn,tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn andtrietazine. Of note is a compound of the invention mixed with atrazine,bromoxynil or metribuzin.

“AHAS inhibitors” (b2) are chemical compounds that inhibit acetohydroxyacid synthase (AHAS), also known as acetolactate synthase (ALS), andthus kill plants by inhibiting the production of the branched-chainaliphatic amino acids such as valine, leucine and isoleucine, which arerequired for protein synthesis and cell growth. Examples of AHASinhibitors include amidosulfuron, azimsulfuron, bensulfuron-methyl,bispyribac-sodium, cloransulam-methyl, chlorimuron-ethyl, chlorsulfuron,cinosulfuron, cyclosulfamuron, diclosulam, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium,flumetsulam, flupyrsulfuron-methyl, flupyrsulfuron-sodium,foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox,imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron,iodosulfuron-methyl (including sodium salt), iofensulfuron(2-iodo-N-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide),mesosulfuron-methyl, metazosulfuron(3-chloro-4-(5,6-dihydro-5-methyl-1,4,2-dioxazin-3-yl)-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-1-methyl-1H-pyrazole-5-sulfonamide),metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, penoxsulam,primisulfuron-methyl, propoxycarbazone-sodium, propyri sulfuron(2-chloro-N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide),prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid,pyriminobac-methyl, pyrithiobac-sodium, rimsulfuron,sulfometuron-methyl, sulfosulfuron, thiencarbazone,thifensulfuron-methyl, triafamone(N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide),triasulfuron, tribenuron-methyl, trifloxysulfuron (including sodiumsalt), triflusulfuron-methyl and tritosulfuron. Of note is a compound ofthe invention mixed with nicosulfuron, flupyrsulfuron or chlorimuron.

“ACCase inhibitors” (b3) are chemical compounds that inhibit theacetyl-CoA carboxylase enzyme, which is responsible for catalyzing anearly step in lipid and fatty acid synthesis in plants. Lipids areessential components of cell membranes, and without them, new cellscannot be produced. The inhibition of acetyl CoA carboxylase and thesubsequent lack of lipid production leads to losses in cell membraneintegrity, especially in regions of active growth such as meristems.Eventually shoot and rhizome growth ceases, and shoot meristems andrhizome buds begin to die back. Examples of ACCase inhibitors includealloxydim, butroxydim, clethodim, clodinafop, cycloxydim, cyhalofop,diclofop, fenoxaprop, fluazifop, haloxyfop, pinoxaden, profoxydim,propaquizafop, quizalofop, sethoxydim, tepraloxydim and tralkoxydim,including resolved forms such as fenoxaprop-P, fluazifop-P, haloxyfop-Pand quizalofop-P and ester forms such as clodinafop-propargyl,cyhalofop-butyl, diclofop-methyl and fenoxaprop-P-ethyl. Of note is acompound of the invention mixed with pinoxaden or quizalofop.

Auxin is a plant hormone that regulates growth in many plant tissues.“Auxin mimics” (b4) are chemical compounds mimicking the plant growthhormone auxin, thus causing uncontrolled and disorganized growth leadingto plant death in susceptible species. Examples of auxin mimics includeaminocyclopyrachlor(6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid) and itsmethyl and ethyl esters and its sodium and potassium salts,aminopyralid, benazolin-ethyl, chloramben, clacyfos, clomeprop,clopyralid, dicamba, 2,4-D, 2,4-DB, dichlorprop, fluroxypyr, halauxifen(4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylicacid), halauxifen-methyl (methyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-2-pyridinecarboxylate),MCPA, MCPB, mecoprop, picloram, quinclorac, quinmerac, 2,3,6-TBA,triclopyr, and methyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate.Of note is a compound of the invention mixed with dicamba.

“EPSP synthase inhibitors” (b5) are chemical compounds that inhibit theenzyme, 5-enol-pyruvylshikimate-3-phosphate synthase, which is involvedin the synthesis of aromatic amino acids such as tyrosine, tryptophanand phenylalanine. EPSP inhibitor herbicides are readily absorbedthrough plant foliage and translocated in the phloem to the growingpoints. Glyphosate is a relatively nonselective postemergence herbicidethat belongs to this group. Glyphosate includes esters and salts such asammonium, isopropylammonium, potassium, sodium (including sesquisodium)and trimesium (alternatively named sulfosate).

“Photosystem I electron diverters” (b6) are chemical compounds thataccept electrons from Photosystem I, and after several cycles, generatehydroxyl radicals. These radicals are extremely reactive and readilydestroy unsaturated lipids, including membrane fatty acids andchlorophyll. This destroys cell membrane integrity, so that cells andorganelles “leak”, leading to rapid leaf wilting and desiccation, andeventually to plant death. Examples of this second type ofphotosynthesis inhibitor include diquat and paraquat.

“PPO inhibitors” (b7) are chemical compounds that inhibit the enzymeprotoporphyrinogen oxidase, quickly resulting in formation of highlyreactive compounds in plants that rupture cell membranes, causing cellfluids to leak out. Examples of PPO inhibitors includeacifluorfen-sodium, azafenidin, benzfendizone, bifenox, butafenacil,carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl,fluazolate, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin,fluoroglycofen-ethyl, fluthiacet-methyl, fomesafen, halosafen, lactofen,oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil,pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin,trifludimoxazin(dihydro-1,5-dimehyl-6-thioxo-3-[2,2,7-trifluoro-3,4-dihydro-3-oxo-4-(2-propyn-1-yl)-2H-1,4-benzoxazin-6-yl]-1,3,5-triazine-2,4(1H,3H)-dione)and tiafenacil (methylN-[2-[[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1-oxopropyl]-β-alaninate).

“GS inhibitors” (b8) are chemical compounds that inhibit the activity ofthe glutamine synthetase enzyme, which plants use to convert ammoniainto glutamine. Consequently, ammonia accumulates and glutamine levelsdecrease. Plant damage probably occurs due to the combined effects ofammonia toxicity and deficiency of amino acids required for othermetabolic processes. The GS inhibitors include glufosinate and itsesters and salts such as glufosinate-ammonium and other phosphinothricinderivatives, glufosinate-P((2S)-2-amino-4-(hydroxymethylphosphinyl)butanoic acid) and bilanaphos.

“VLCFA elongase inhibitors” (b9) are herbicides having a wide variety ofchemical structures, which inhibit the elongase. Elongase is one of theenzymes located in or near chloroplasts which are involved inbiosynthesis of VLCFAs. In plants, very-long-chain fatty acids are themain constituents of hydrophobic polymers that prevent desiccation atthe leaf surface and provide stability to pollen grains. Such herbicidesinclude acetochlor, alachlor, anilofos, butachlor, cafenstrole,dimethachlor, dimethenamid, diphenamid, fenoxasulfone(3-[[(2,5-dichloro-4-ethoxyphenyl)methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole), fentrazamide, flufenacet, indanofan,mefenacet, metazachlor, metolachlor, naproanilide, napropamide,napropamide-M ((2R)—N,N-diethyl-2-(1-naphthalenyloxy)propanamide),pethoxamid, piperophos, pretilachlor, propachlor, propisochlor,pyroxasulfone, and thenylchlor, including resolved forms such asS-metolachlor and chloroacetamides and oxyacetamides. Of note is acompound of the invention mixed with flufenacet.

“Auxin transport inhibitors” (b10) are chemical substances that inhibitauxin transport in plants, such as by binding with an auxin-carrierprotein. Examples of auxin transport inhibitors include diflufenzopyr,naptalam (also known as N-(1-naphthyl)phthalamic acid and2-[(1-naphthalenylamino)carbonyl]benzoic acid).

“PDS inhibitors” (b1) are chemical compounds that inhibit carotenoidbiosynthesis pathway at the phytoene desaturase step. Examples of PDSinhibitors include beflubutamid, diflufenican, fluridone,flurochloridone, flurtamone norflurzon and picolinafen.

“HPPD inhibitors” (b12) are chemical substances that inhibit thebiosynthesis of synthesis of 4-hydroxyphenyl-pyruvate dioxygenase.Examples of HPPD inhibitors include benzobicyclon, benzofenap,bicyclopyrone(4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one),fenquinotrione(2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione),isoxachlortole, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate,pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate(1-[[1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl]oxy]ethylmethyl carbonate), topramezone,5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone,4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone,4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione,5-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-(3-methoxyphenyl)-3-(3-methoxypropyl)-4(3H)-pyrimidinone,2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamideand 2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide. Ofnote is a compound of the invention mixed with mesotrione orpyrasulfatole.

“HST inhibitors” (b13) disrupt a plant's ability to converthomogentisate to 2-methyl-6-solanyl-1,4-benzoquinone, thereby disruptingcarotenoid biosynthesis. Examples of HST inhibitors includecyclopyrimorate(6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-morpholinecarboxylate), haloxydine, pyriclor,3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one,7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-oneand 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone.

HST inhibitors also include compounds of Formulae A and B.

-   -   wherein R^(d1) is H, Cl or CF₃; R^(d2) is H, Cl or Br; R^(d3) is        H or Cl; R^(d4) is H, Cl or CF₃; R^(d5) is CH₃, CH₂CH₃ or        CH₂CHF₂; and R^(d6) is OH, or —OC(═O)-i-Pr; and R^(e1) is H, F,        Cl, CH₃ or CH₂CH₃; R^(e2) is H or CF₃; R^(e3) is H, CH₃ or        CH₂CH₃; R^(e4) is H, F or Br; R^(e5) is Cl, CH₃, CF₃, OCF₃ or        CH₂CH₃; R^(e6) is H, CH₃, CH₂CHF₂ or C≡CH; R^(e7) is OH,        —OC(═O)Et, —OC(═O)-i-Pr or —OC(═O)-t-Bu; and A^(e8) is N or CH.

“Cellulose biosynthesis inhibitors” (b14) inhibit the biosynthesis ofcellulose in certain plants. They are most effective when appliedpreemergence or early postemergence on young or rapidly growing plants.Examples of cellulose biosynthesis inhibitors include chlorthiamid,dichlobenil, flupoxam, indaziflam(N²-[(1R,2S)-2,3-dihydro-2,6-dimethyl-1H-inden-1-yl]-6-(1-fluoroethyl)-1,3,5-triazine-2,4-diamine),isoxaben and triaziflam.

“Other herbicides” (b15) include herbicides that act through a varietyof different modes of action such as mitotic disruptors (e.g.,flamprop-M-methyl and flamprop-M-isopropyl), organic arsenicals (e.g.,DSMA, and MSMA), 7,8-dihydropteroate synthase inhibitors, chloroplastisoprenoid synthesis inhibitors and cell-wall biosynthesis inhibitors.Other herbicides include those herbicides having unknown modes of actionor do not fall into a specific category listed in (b1) through (b14) oract through a combination of modes of action listed above. Examples ofother herbicides include aclonifen, asulam, amitrole, bromobutide,cinmethylin, clomazone, cumyluron, daimuron, difenzoquat, etobenzanid,fluometuron, flurenol, fosamine, fosamine-ammonium, dazomet, dymron,ipfencarbazone(1-(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5-oxo-4H-1,2,4-triazole-4-carboxamide),metam, methyldymron, oleic acid, oxaziclomefone, pelargonic acid,pyributicarb and5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole.

“Herbicide safeners” (b16) are substances added to a herbicideformulation to eliminate or reduce phytotoxic effects of the herbicideto certain crops. These compounds protect crops from injury byherbicides but typically do not prevent the herbicide from controllingundesired vegetation. Examples of herbicide safeners include but are notlimited to benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil,cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate,dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim,furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate,methoxyphenone, naphthalic anhydride, oxabetrinil,N-(aminocarbonyl)-2-methylbenzenesulfonamide andN-(aminocarbonyl)-2-fluorobenzenesulfonamide,1-bromo-4-[(chloromethyl)sulfonyl]benzene,2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191),4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660),2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamide.

The compounds of Formula 1 can be prepared by general methods known inthe art of synthetic organic chemistry. One or more of the followingmethods and variations as described in Schemes 1-5 can be used toprepare the compounds of Formula 1. The definitions of R¹, R², R³, R⁴,R⁵, Q¹, Q², Y¹, and Y² in the compounds of Formulae 1-6 below are asdefined above in the Summary of the Invention unless otherwise noted.Compounds of Formulae 1a-1e are various subsets of the compounds ofFormula 1, and all substituents for Formulae 1a-1e are as defined abovefor Formula 1 unless otherwise noted.

As shown in Scheme 1 compounds of Formula 1a (i.e. Formula 1 wherein R⁴is H, and Y¹ and Y² are 0) can be prepared by reaction of acids ofFormula 2 with amines of Formula 3 in the presence of a dehydrativecoupling reagent such as propylphosphonic anhydride (T3P),dicyclohexylcarbodiimide (DCC),N-(3-dimethylaminopropyl)-N-ethylcarbodiimide, N,N-carbonyldiimidazole(EDC), 2-chloro-1,3-dimethylimidazolium chloride or2-chloro-1-methylpyridinium iodide (Mukaiyama's Reagent).Polymer-supported reagents, such as polymer-supportedcyclohexylcarbodiimide, are also suitable. These reactions are typicallyrun at temperatures ranging from 0-60° C. in a solvent such as, but notlimited to, dichloromethane, acetonitrile, N,N-dimethylformamide orethyl acetate in the presence of a base such as triethylamine,N,N-diisopropylamine, or 1,8-diazabicyclo[5.4.0]undec-7-ene. See OrganicProcess Research & Development 2009, 13, 900-906 for coupling conditionsemploying propylphosphonic anhydride. Substituents in the 3- and4-positions of the furanone ring of compounds of Formula 1a, i.e.C(O)N(Q²)(R¹) and Q¹, respectively, are predominantly in the transconfiguration.

As shown in Scheme 2 compounds of Formula 2 can be prepared byhydrolysis of esters of Formula 4 by methods well known to those skilledin the art. Hydrolysis is carried out with aqueous base or aqueous acid,typically in the presence of a co-solvent. Suitable bases for thereaction include, but are not limited to, hydroxides such as lithium,sodium and potassium hydroxide and carbonates such as sodium andpotassium carbonate. Suitable acids for the reaction include, but arenot limited to, inorganic acids such as hydrochloric acid, hydrobromicacid and sulfuric acid, and organic acids such as acetic acid andtrifluoroacetic acid. A wide variety of co-solvents are suitable for thereaction including, but not limited to, methanol, ethanol andtetrahydrofuran. The reaction is conducted at temperatures ranging from−20° C. to the boiling point of the solvent, and typically from 0 to100° C. A representative procedure can be found in Ollis and co-workers:J. Chem. Soc Perkin 1 1975, 1480.

Esters of Formula 4 can be prepared by the reaction of epoxides ofFormula 5 with substituted malonates of Formula 6. This transformationrequires the presence of an acid acceptor such as sodium hydride, sodiummethoxide or sodium ethoxide. Other alkali alkoxides and hydrides alsomay be successfully employed. The reaction can be carried out in avariety of solvents including protic solvents such as methanol andethanol as well as aprotic solvents such as N,N-dimethylformamide,dimethyl sulfoxide and tetrahydrofuran. Temperatures from 0 OC to theboiling point of the solvent can be employed. Typical reactionconditions can be found in Indian Journal of Chemistry, Section B:Organic Chemistry Including Medicinal Chemistry 1981, 20B (9), 807-8.Epoxides may be replaced in this reaction by 1,2-cyclic sulfites asreported by Nymann and Svendsen in Acta Chemica Scandinavica 1998,52(3), 338-349. Another route to esters of Formula 4 has been reportedby Yamada and coworkers in Journal of Organic Chemistry 2008, 73(24),9535-9538. Alternatively, esters of Formula 4 can also be made by amethod reported by Tran and colleagues in Bioorganic & MedicinalChemistry Letters 2008, 18(3), 1124-1130. Epoxides of Formula 5 are wellknown in the literature and can be prepared by the well-known olefinepoxidation reaction of known or commercially available styrenes.Alternatively the reaction of sulfoxonium ylides with known orcommercially available aldehydes also can be employed to synthesizeepoxides of Formula 5 as reviewed by Gobolobov and coworkers inTetrahedron 1987, 43, 2609.

As shown in Scheme 4, mixtures of compounds of Formula 1b (i.e. Formula1 wherein R⁵ is H, R⁴ is halogen and Y¹ and Y² are 0) and Formula 1c(i.e. Formula 1 wherein R⁴ is H, R⁵ is halogen and Y¹ and Y² are 0) canbe prepared by reacting compounds of Formula 1a with a halogen source ina solvent, in the presence or absence of an initiator. Suitable halogensources for this reaction include bromine, chlorine,N-chlorosuccinimide, N-bromosuccinimide and N-iodosuccinimide. Suitableinitiators for this reaction include 2,2′-azobisisobutyronitrile (AIBN)and benzoyl peroxide. Typically, the reaction is carried out in solventssuch as dichloromethane in the range of from 0° C. to the boiling pointof the solvent.

As shown in Scheme 5, compounds of Formula 1e (i.e. Formula 1 wherein Y¹and Y² are S) can be prepared by reacting compounds of Formula 1d withat least two equivalents of a thionation reagent such as Lawesson'sreagent, tetraphosphorus decasulfide or diphosphorus pentasulfide in asolvent such as tetrahydrofuran or toluene. Typically, the reaction iscarried out at temperatures ranging from 0 to 115° C. One skilled in theart recognizes that using less than two equivalents of the thionatingreagent can provide mixtures comprising Formula 1 products wherein Y¹ isO and Y² is S, or Y¹ is S and Y² is O, which can be separated byconventional methods such as chromatography and crystallization.

It is recognized by one skilled in the art that various functionalgroups can be converted into others to provide different compounds ofFormula 1. For a valuable resource that illustrates the interconversionof functional groups in a simple and straightforward fashion, seeLarock, R. C., Comprehensive Organic Transformations: A Guide toFunctional Group Preparations, 2nd Ed, Wiley-VCH, New York, 1999. Forexample, intermediates for the preparation of compounds of Formula 1 maycontain aromatic nitro groups, which can be reduced to amino groups, andthen be converted via reactions well known in the art such as theSandmeyer reaction, to various halides, providing compounds ofFormula 1. The above reactions can also in many cases be performed inalternate order

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of Formula 1 may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P. G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas depicted in any individual scheme, it may be necessary to performadditional routine synthetic steps not described in detail to completethe synthesis of compounds of Formula 1. One skilled in the art willalso recognize that it may be necessary to perform a combination of thesteps illustrated in the above schemes in an order other than thatimplied by the particular presented to prepare the compounds of Formula1.

One skilled in the art will also recognize that compounds of Formula 1and the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following non-limiting Examples are illustrative ofthe invention. Steps in the following Examples illustrate a procedurefor each step in an overall synthetic transformation, and the startingmaterial for each step may not have necessarily been prepared by aparticular preparative run whose procedure is described in otherExamples or Steps. Percentages are by weight except for chromatographicsolvent mixtures or where otherwise indicated. Parts and percentages forchromatographic solvent mixtures are by volume unless otherwiseindicated. ¹H NMR spectra are reported at 400 MHz in ppm downfield fromtetramethylsilane; “s” means singlet, “d” means doublet, “t” meanstriplet, “q” means quartet and “m” means multiplet.

Synthesis Example 1 Preparation of4-(4-fluorophenyl)tetrahydro-2-oxo-N-[2-(trifluoromethyl)phenyl)]-3-furancarboxamide(Compound 6) Step A: Preparation of4-(4-fluorophenyl)tetrahydro-2-oxo-3-furancarboxylic acid ethyl ester

To a 250 mL two neck round bottom flask was added sodium metal (0.99 g,0.043 mol) in ethanol (60 mL) and then diethyl malonate (6.6 g, 0.041mol) was added slowly at room temperature. The reaction mixture wasstirred for 15 min at room temperature, the temperature was then raisedto 40° C. and 2-(4-fluorophenyl)oxirane (5.0 g, 0.036 mmol) was addedslowly to the reaction mixture over 2 h. The reaction mixture was thenstirred for 18 h at room temperature. The progress of the reaction wasmonitored by TLC analysis. After completion of reaction, the reactionmixture was neutralized using 1M aqueous hydrochloric acid and thenconcentrated to a residue. The resulting residue was diluted with waterand then extracted with ethyl acetate (3×300 mL). The combined organiclayers were washed with water, dried over anhydrous Na₂SO₄ andconcentrated under reduced pressure to afford crude compound. This waspurified by column chromatography using 20% ethyl acetate: petroleumether to afford the title compound of Step A (3.0 g) as a colorlessliquid.

¹H NMR (DMSO-d₆) δ 7.48-7.44 (m, 2H), 7.23-7.19 (t, J=8.8 Hz, 2H),4.68-4.66 (t, J=7.6 Hz, 1H), 4.22-4.19 (m, 2H), 4.17 (m, 1H), 4.15-4.11(q, 2H), 1.17-1.14 (t, 3H).

Step B: Preparation of4-(4-fluorophenyl)tetrahydro-2-oxo-3-furancarboxylic acid

To a solution of the compound from Step A (1.3 g, 5.158 mmol) in water(13 mL) was added potassium hydroxide (1.73 g, 30.957 mmol) and thereaction mixture was stirred at room temperature for 2 h. The progressof the reaction was monitored by TLC analysis. After completion of thereaction, the reaction mixture was cooled to 0° C. and concentratedhydrochloric acid was added and the resulting mixture was stirred for 15min. The precipitate was filtered to afford the title compound of Step B(750 mg) as white solid melting at 138-140° C.

¹H NMR (DMSO-d₆) δ 13.2 (s, 1H), 7.46-7.45 (m, 2H), 7.44-7.21 (t, 2H),4.67-4.63 (t, J=7.6 Hz, 1H), 4.19-4.01 (m, 3H).

Step C: Preparation of4-(4-fluorophenyl)tetrahydro-2-oxo-N-[2-(trifluoromethyl)phenyl)]-3-furancarboxamide

To a solution of the compound from Step B (200 mg, 0.892 mmol) inN,N-dimethylformamide (3 mL) was added N,N-diisopropylethylamine (138mg, 1.071 mmol) followed by HATU[1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4, 5-b]pyridinium3-oxide hexafluorophosphate] (408 mg, 1.071 mmol) and2-(trifluoromethyl)aniline (99 mg, 0.892 mmol). The reaction mixture wasthen stirred at room temperature for 6 h. The progress of the reactionwas monitored by thin layer chromatography analysis. After completion ofthe reaction, the reaction mixture was poured into water (15 mL) andextracted with ethyl acetate (3×10 mL). The combined organic layers werewashed with water followed by brine solution, dried over anhydrousNa₂SO₄ and concentrated under reduced pressure to afford crude compound.This was purified by column chromatography using 30% ethyl acetate inpetroleum ether to afford the title compound of Example 1, Compound 6 inIndex Table A (100 mg) as white solid melting at 144-146° C.

¹H NMR (DMSO-d₆) δ 10.08 (s, 1H), 7.73-7.66 (m, 2H), 7.47-7.43 (m, 4H),7.24-7.20 (t, 2H), 4.74-4.70 (t, J=7.2 Hz, 1H), 4.21-4.19 (m, 3H).

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 40 can be prepared. Thefollowing abbreviations are used in the Tables which follow: Me meansmethyl, i-Pr means isopropyl and Bu means butyl.

TABLE 1

Q² is Ph(2-F); and Q¹ is Ph(3-Cl) Ph(3-F) Ph(3-Br) Ph(3-Me) Ph(3-CF₃)Ph(3-CH₂CF₃) Ph(3-OCF₃) Ph(3-OCF₂H) Ph(3-O-i-Pr) Ph(3-OMe)Ph(3-OCF₂CF₂H) Ph(2-Cl) Ph(2-F) Ph(2-Br) Ph(2-Me) Ph(2-CF₃) Ph(2-OCF₃)Ph(2-OCF₂H) Ph(2-OMe) Ph(2-OCF₂CF₂H) Ph(2-CH₂CF₃) Ph(2-O-i-Pr) Ph(4-Cl)Ph(4-F) Ph(4-Br) Ph(4-Me) Ph(4-CF₃) Ph(4-OCF₃) Ph(4-OCF₂H) Ph(4-OMe)Ph(4-CH₂CF₃) Ph(4-O-i-Pr) Ph(4-OCF₂CF₂H) Ph(2,3-di-F) Ph(2,4-di-F)Ph(2,5-di-F) Ph(2,6-di-F) Ph(3,4-di-F) Ph(3,5-di-F) Ph(3-Me,4-F)Ph(3-F,4-Me) Ph(3-CF₃,4-F) Ph(3-F,4-CF₃) Ph(2,3,4-tri-F) Ph(3,4,5-tri-F)2-Pyridinyl 2-Pyridinyl(6-F) 2-Pyridinyl(6-CF₃) 2-Pyridinyl(6-Me)2-Pyridinyl(5-F) 2-Pyridinyl(5-CF₃) 2-Pyridinyl(5-Me) 2-Pyridinyl(4-F)2-Pyridinyl(4-CF₃) 2-Pyridinyl(4-Me) 2-Pyridinyl(3-F) 2-Pyridinyl(3-CF₃)2-Pyridinyl(3-Me) 3-Pyridinyl 3-Pyridinyl(6-F) 3-Pyridinyl(6-CF₃)3-Pyridinyl(6-Me) 3-Pyridinyl(5-F) 3-Pyridinyl(5-CF₃) 3-Pyridinyl(5-Me)3-Pyridinyl(4-F) 3-Pyridinyl(4-CF₃) 3-Pyridinyl(4-Me) 3-Pyridinyl(2-F)3-Pyridinyl(2-CF₃) 3-Pyridinyl(2-Me) 4-Pyridinyl 4-Pyridinyl(6-F)4-Pyridinyl(6-CF₃) 4-Pyridinyl(6-Me) 4-Pyridinyl(5-F) 4-Pyridinyl(5-CF₃)4-Pyridinyl(5-Me) 4-Pyridinyl(3-F) 4-Pyridinyl(3-CF₃) 4-Pyridinyl(3-Me)4-Pyridinyl(2-F) 4-Pyridinyl(2-CF₃) 4-Pyridinyl(2-Me) 2-Thienyl2-Thienyl(4-CF₃) 2-Thienyl(5-CF₃) 3-Thienyl 3-Thienyl(4-CF₃)3-Thienyl(5-CF₃) 2-Furyl 2-Furyl(4-CF₃) 2-Furyl(5-CF₃) 3-Furyl3-Furyl(4-CF₃) 3-Furyl(5-CF₃) Pyrazol-1-yl Pyrazol-1-yl(4-CF₃)Imidazol-1-yl Imidazol-1-yl(4-CF₃) Imidazol-1-yl(2-CF₃)Imidazol-2-yl(1-Me) Imidazol-4-yl(1-Me) Imidazol-4-yl(3-Me)Pyrazol-4-yl(1-Me) Triazol-4-yl(1-Me) Triazol-4-yl(2-Me)Triazol-2-yl(4-Me) Triazol-1-yl(4-Me) Pyrazin-2-yl Pyrazin-2-yl(5-CF₃)Pyrimidin-2-yl Pyrimidin-2-yl(5-CF₃) Pyrimidin-5-ylPyrimidin-5-yl(2-CF₃) 1,3,5-Triazin-2-yl Thiazol-2-ylThiazol-2-yl(5-CF₃) Thiazol-5-yl Thiazol-5-yl(2-CF₃) Oxazol-2-ylOxazol-2-yl(5-CF₃) Oxazol-5-yl Oxazol-5-yl(2-CF₃) Isothiazol-5-ylIsothiazol-5-yl(3-CF₃) Isothiazol-3-yl Isothiazol-3-yl(5-CF₃)Isoxazol-5-yl Isoxazol-5-yl(3-CF₃) Isoxazol-3-yl Isoxazol-3-yl(5-CF₃)Tetrazol-1-yl Tetrazol-1-yl(5-Me) Tetrazol-5-yl(1-Me) 1,2,4-Triazol-1-yl1,3,4-Oxadiazol-2-yl 1,3,4-Thiadiazol-2-yl 1,2,4-Oxadiazol-3-yl1,2,4-Thiadiazol-3-yl Tetrahydropyran-2-yl Tetrahydropyran-3-ylTetrahydrofuran-2-yl Tetrahydrofuran-3-yl 1,3-Dioxolan-4-yl2,2-di-Fluoro-1,3-Dioxolan-4-yl 1,3-Dithiolan-4-yl 1,4-Dioxolan-2-yl1,4-Dithiolan-2-yl 1-Naphthyl 2-Naphthyl Benzofuran-2-ylBenzothiophen-2-yl 1,3-Benzoxazol-2-yl 1,3-Benzthiazol-2-yl 7-QuinolylIndazol-1-yl Benzimidazol-1-yl Indol-1-yl Pyrrolo[2,3-c]pyridin-1-ylPh(3-OCH₂-c-Pr) Ph(2-OCH₂-c-Pr) Ph(4-OCH₂CH₂CH₂CH₂-c-hex) Ph(CH₂-c-Pr)Ph(4-CH₂CH₂CH₂CH₂-c-hex) Ph(2-(3,3-dichloroallyloxy))Ph(2-methoxyethoxy) Ph(3-propoxypropoxy) Ph(2-CH₂CH₂SCH₃)Ph(2-CH₂CH₂SOCH₃) Ph(2-CH₂CH₂SO₂CH₃) Ph(3-SMe) Ph(3-SCF₃) Ph(3-S-c-Pr)Ph(3-SOMe) Ph(3-SOCF₃) Ph(3-SO-c-Pr) Ph(3-SO₂Me) Ph(3-SO₂CF₃)Ph(3-SO₂-c-Pr) Ph(3-propargyl) Ph(3-(2-Butynyl)) Ph(2-CH₂CH₂OCH₂CH₃)Ph(2-C(═O)CH₃) Ph(2-OC(═O)CH₃) Ph(3-OC(═O)CH₃) Ph(2-OC(═O)CF₃)Ph(3-OC(═O)CF₃)

Table 2 is constructed in the same manner except that the Row Heading“Q² is Ph(2-F); and Q¹ is” is replaced with the Row Heading listed forTable 2 below (i.e. “Q² is Ph(2,3-di-F); and Q¹ is”). Therefore thefirst entry in Table 2 is a compound of Formula 1 wherein Q² isPh(2,3-di-F); and Q¹ is; and Q¹ is Ph(3-Cl) (i.e. 3-chlorophenyl).Tables 3 through 10 are constructed similarly.

Table Row Heading 2 Q² is Ph(2,3-di-F); and Q¹ is 3 Q² is Ph(2,4-di-F);and Q¹ is 4 Q² is Ph(2,3,4-tri-F); and Q¹ is 5 Q² is Ph(2-CF₃); and Q¹is 6 Q² is Ph(2-Me); and Q¹ is 7 Q² is Ph(2-NO₂); and Q¹ is 8 Q² isPh(2-Cl); and Q¹ is 9 Q² is Ph(2-SO₂Me); and Q¹ is 10 Q² isPh(2-F,3-Cl); and Q¹ is

Table 11

Table 11 is constructed the same way as Table 1 above, except thestructure is replaced with the following:

Tables 12 Through 20

This disclosure also includes Tables 12 through 20, each Table isconstructed in the same fashion as Tables 2 through 10 above, exceptthat the structure is replaced with the structure in Table 11 above.

Table 21

Table 21 is constructed the same way as Table 1 above, except thestructure is replaced with the following:

Tables 22 Through 30

This disclosure also includes Tables 22 through 30, each Table isconstructed in the same fashion as Tables 2 through 10 above, exceptthat the structure is replaced with the structure in Table 21 above.

Table 31

Table 31 is constructed the same way as Table 1 above, except thestructure is replaced with the following:

Tables 32 Through 40

This disclosure also includes Tables 32 through 40, each Table isconstructed in the same fashion as Tables 2 through 10 above, exceptthat the structure is replaced with the structure in Table 31 above.

A compound of this invention will generally be used as a herbicidalactive ingredient in a composition, i.e. formulation, with at least oneadditional component selected from the group consisting of surfactants,solid diluents and liquid diluents, which serves as a carrier. Theformulation or composition ingredients are selected to be consistentwith the physical properties of the active ingredient, mode ofapplication and environmental factors such as soil type, moisture andtemperature.

Useful formulations include both liquid and solid compositions. Liquidcompositions include solutions (including emulsifiable concentrates),suspensions, emulsions (including microemulsions, oil-in-wateremulsions, flowable concentrates and/or suspoemulsions) and the like,which optionally can be thickened into gels. The general types ofaqueous liquid compositions are soluble concentrate, suspensionconcentrate, capsule suspension, concentrated emulsion, microemulsion,oil-in-water emulsion, flowable concentrate and suspo-emulsion. Thegeneral types of nonaqueous liquid compositions are emulsifiableconcentrate, microemulsifiable concentrate, dispersible concentrate andoil dispersion.

The general types of solid compositions are dusts, powders, granules,pellets, prills, pastilles, tablets, filled films (including seedcoatings) and the like, which can be water-dispersible (“wettable”) orwater-soluble. Films and coatings formed from film-forming solutions orflowable suspensions are particularly useful for seed treatment. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or “overcoated”). Encapsulationcan control or delay release of the active ingredient. An emulsifiablegranule combines the advantages of both an emulsifiable concentrateformulation and a dry granular formulation. High-strength compositionsare primarily used as intermediates for further formulation.

Sprayable formulations are typically extended in a suitable mediumbefore spraying. Such liquid and solid formulations are formulated to bereadily diluted in the spray medium, usually water, but occasionallyanother suitable medium like an aromatic or paraffinic hydrocarbon orvegetable oil. Spray volumes can range from about from about one toseveral thousand liters per hectare, but more typically are in the rangefrom about ten to several hundred liters per hectare. Sprayableformulations can be tank mixed with water or another suitable medium forfoliar treatment by aerial or ground application, or for application tothe growing medium of the plant. Liquid and dry formulations can bemetered directly into drip irrigation systems or metered into the furrowduring planting.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersibleand Water- 0.001-90 0-99.999 0-15 soluble Granules, Tablets and PowdersOil Dispersions, Suspensions,    1-50 40-99    0-50 Emulsions, Solutions(including Emulsifiable Concentrates) Dusts    1-25 70-99    0-5 Granules and Pellets 0.001-99 5-99.999 0-15 High Strength Compositions  90-99 0-10    0-2 

Solid diluents include, for example, clays such as bentonite,montmorillonite, attapulgite and kaolin, gypsum, cellulose, titaniumdioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose),silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodiumcarbonate and bicarbonate, and sodium sulfate. Typical solid diluentsare described in Watkins et al., Handbook of Insecticide Dust Diluentsand Carriers, 2nd Ed., Dorland Books, Caldwell, N.J.

Liquid diluents include, for example, water, N,N-dimethylalkanamides(e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide,N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates(e.g., triethyl phosphate), ethylene glycol, triethylene glycol,propylene glycol, dipropylene glycol, polypropylene glycol, propylenecarbonate, butylene carbonate, paraffins (e.g., white mineral oils,normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes,glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons,dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones suchas cyclohexanone, 2-heptanone, isophorone and4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexylacetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetateand isobornyl acetate, other esters such as alkylated lactate esters,dibasic esters, alkyl and aryl benzoates and γ-butyrolactone, andalcohols, which can be linear, branched, saturated or unsaturated, suchas methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutylalcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecylalcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecylalcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol,diacetone alcohol, cresol and benzyl alcohol. Liquid diluents alsoinclude glycerol esters of saturated and unsaturated fatty acids(typically C₆-C₂₂), such as plant seed and fruit oils (e.g., oils ofolive, castor, linseed, sesame, corn (maize), peanut, sunflower,grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palmkernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, codliver oil, fish oil), and mixtures thereof. Liquid diluents also includealkylated fatty acids (e.g., methylated, ethylated, butylated) whereinthe fatty acids may be obtained by hydrolysis of glycerol esters fromplant and animal sources, and can be purified by distillation. Typicalliquid diluents are described in Marsden, Solvents Guide, 2nd Ed.,Interscience, New York, 1950.

The solid and liquid compositions of the present invention often includeone or more surfactants. When added to a liquid, surfactants (also knownas “surface-active agents”) generally modify, most often reduce, thesurface tension of the liquid. Depending on the nature of thehydrophilic and lipophilic groups in a surfactant molecule, surfactantscan be useful as wetting agents, dispersants, emulsifiers or defoamingagents.

Surfactants can be classified as nonionic, anionic or cationic. Nonionicsurfactants useful for the present compositions include, but are notlimited to: alcohol alkoxylates such as alcohol alkoxylates based onnatural and synthetic alcohols (which may be branched or linear) andprepared from the alcohols and ethylene oxide, propylene oxide, butyleneoxide or mixtures thereof; amine ethoxylates, alkanolamides andethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylatedsoybean, castor and rapeseed oils; alkylphenol alkoxylates such asoctylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenolethoxylates and dodecyl phenol ethoxylates (prepared from the phenolsand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); block polymers prepared from ethylene oxide or propylene oxideand reverse block polymers where the terminal blocks are prepared frompropylene oxide; ethoxylated fatty acids; ethoxylated fatty esters andoils; ethoxylated methyl esters; ethoxylated tristyrylphenol (includingthose prepared from ethylene oxide, propylene oxide, butylene oxide ormixtures thereof); fatty acid esters, glycerol esters, lanolin-basedderivatives, polyethoxylate esters such as polyethoxylated sorbitanfatty acid esters, polyethoxylated sorbitol fatty acid esters andpolyethoxylated glycerol fatty acid esters; other sorbitan derivativessuch as sorbitan esters; polymeric surfactants such as randomcopolymers, block copolymers, alkyd peg (polyethylene glycol) resins,graft or comb polymers and star polymers; polyethylene glycols (pegs);polyethylene glycol fatty acid esters; silicone-based surfactants; andsugar-derivatives such as sucrose esters, alkyl polyglycosides and alkylpolysaccharides.

Useful anionic surfactants include, but are not limited to: alkylarylsulfonic acids and their salts; carboxylated alcohol or alkylphenolethoxylates; diphenyl sulfonate derivatives; lignin and ligninderivatives such as lignosulfonates; maleic or succinic acids or theiranhydrides; olefin sulfonates; phosphate esters such as phosphate estersof alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates andphosphate esters of styryl phenol ethoxylates; protein-basedsurfactants; sarcosine derivatives; styryl phenol ether sulfate;sulfates and sulfonates of oils and fatty acids; sulfates and sulfonatesof ethoxylated alkylphenols; sulfates of alcohols; sulfates ofethoxylated alcohols; sulfonates of amines and amides such asN,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, anddodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes;sulfonates of naphthalene and alkyl naphthalene; sulfonates offractionated petroleum; sulfosuccinamates; and sulfosuccinates and theirderivatives such as dialkyl sulfosuccinate salts.

Useful cationic surfactants include, but are not limited to: amides andethoxylated amides; amines such as N-alkyl propanediamines,tripropylenetriamines and dipropylenetetramines, and ethoxylated amines,ethoxylated diamines and propoxylated amines (prepared from the aminesand ethylene oxide, propylene oxide, butylene oxide or mixturesthereof); amine salts such as amine acetates and diamine salts;quaternary ammonium salts such as quaternary salts, ethoxylatedquaternary salts and diquaternary salts; and amine oxides such asalkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

Also useful for the present compositions are mixtures of nonionic andanionic surfactants or mixtures of nonionic and cationic surfactants.Nonionic, anionic and cationic surfactants and their recommended usesare disclosed in a variety of published references includingMcCutcheon's Emulsifiers and Detergents, annual American andInternational Editions published by McCutcheon's Division, TheManufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopediaof Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; andA. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition,John Wiley and Sons, New York, 1987.

Compositions of this invention may also contain formulation auxiliariesand additives, known to those skilled in the art as formulation aids(some of which may be considered to also function as solid diluents,liquid diluents or surfactants). Such formulation auxiliaries andadditives may control: pH (buffers), foaming during processing(antifoams such polyorganosiloxanes), sedimentation of activeingredients (suspending agents), viscosity (thixotropic thickeners),in-container microbial growth (antimicrobials), product freezing(antifreezes), color (dyes/pigment dispersions), wash-off (film formersor stickers), evaporation (evaporation retardants), and otherformulation attributes. Film formers include, for example, polyvinylacetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinylacetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers andwaxes. Examples of formulation auxiliaries and additives include thoselisted in McCutcheon's Volume 2: Functional Materials, annualInternational and North American editions published by McCutcheon'sDivision, The Manufacturing Confectioner Publishing Co.; and PCTPublication WO 03/024222.

The compound of Formula 1 and any other active ingredients are typicallyincorporated into the present compositions by dissolving the activeingredient in a solvent or by grinding in a liquid or dry diluent.Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. If the solvent of a liquid compositionintended for use as an emulsifiable concentrate is water-immiscible, anemulsifier is typically added to emulsify the active-containing solventupon dilution with water. Active ingredient slurries, with particlediameters of up to 2,000 m can be wet milled using media mills to obtainparticles with average diameters below 3 m. Aqueous slurries can be madeinto finished suspension concentrates (see, for example, U.S. Pat. No.3,060,084) or further processed by spray drying to formwater-dispersible granules. Dry formulations usually require dry millingprocesses, which produce average particle diameters in the 2 to 10 mrange. Dusts and powders can be prepared by blending and usuallygrinding (such as with a hammer mill or fluid-energy mill). Granules andpellets can be prepared by spraying the active material upon preformedgranular carriers or by agglomeration techniques. See Browning,“Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry'sChemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963,pages 8-57 and following, and WO 91/13546. Pellets can be prepared asdescribed in U.S. Pat. No. 4,172,714. Water-dispersible andwater-soluble granules can be prepared as taught in U.S. Pat. No.4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can beprepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see T. S.Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture”in Pesticide Chemistry and Bioscience, The Food-Environment Challenge,T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th InternationalCongress on Pesticide Chemistry, The Royal Society of Chemistry,Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6,line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No.3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12,15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 andExamples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons,Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8thEd., Blackwell Scientific Publications, Oxford, 1989; and Developmentsin formulation technology, PJB Publications, Richmond, U K, 2000.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Table A. Without further elaboration, it isbelieved that one skilled in the art using the preceding description canutilize the present invention to its fullest extent. The followingExamples are, therefore, to be construed as merely illustrative, and notlimiting of the disclosure in any way whatsoever. Percentages are byweight except where otherwise indicated.

Example A

High Strength Concentrate Compound 6 98.5% silica aerogel 0.5% syntheticamorphous fine silica 1.0%

Example B

Wettable Powder Compound 6 65.0% dodecylphenol polyethylene glycol ether2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0%montmorillonite (calcined) 23.0%

Example C

Granule Compound 6 10.0% attapulgite granules (low volatile matter,0.71/0.30 mm; 90.0% U.S.S. No. 25-50 sieves)

Example D

Extruded Pellet Compound 6 25.0% anhydrous sodium sulfate 10.0% crudecalcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0%calcium/magnesium bentonite 59.0%

Example E

Emulsifiable Concentrate Compound 6 10.0% polyoxyethylene sorbitolhexoleate 20.0% C₆-C₁₀ fatty acid methyl ester 70.0%

Example F

Microemulsion Compound 6 5.0% polyvinylpyrrolidone-vinyl acetatecopolymer 30.0% alkylpolyglycoside 30.0% glyceryl monooleate 15.0% water20.0%

Example G

Suspension Concentrate Compound 6  35% butylpolyoxyethylene/polypropylene block copolymer 4.0% stearicacid/polyethylene glycol copolymer 1.0% styrene acrylic polymer 1.0%xanthan gum 0.1% propylene glycol 5.0% silicone based defoamer 0.1%1,2-benzisothiazolin-3-one 0.1% water 53.7% 

Example H

Emulsion in Water Compound 6 10.0% butyl polyoxyethylene/polypropyleneblock copolymer 4.0% stearic acid/polyethylene glycol copolymer 1.0%styrene acrylic polymer 1.0% xanthan gum 0.1% propylene glycol 5.0%silicone based defoamer 0.1% 1,2-benzisothiazolin-3-one 0.1% aromaticpetroleum based hydrocarbon 20.0 water 58.7%

Example I

Oil Dispersion Compound 6 25% polyoxyethylene sorbitol hexaoleate 15%organically modified bentonite clay 2.5%  fatty acid methyl ester 57.5% 

The present disclosure also includes Formulation Examples A through Iabove except “Compound is 6” in each of the above Examples A through Iis replaced with “Compound 1”, “Compound 2”, “Compound 3”, “Compound 4”,“Compound 5”, “Compound 7”, “Compound 8”, “Compound 9”, “Compound 10”,“Compound 11”, “Compound 12”, “Compound 13”, “Compound 14”, “Compound15”, “Compound 16”, “Compound 17”, “Compound 18”, “Compound 19”,“Compound 20”, “Compound 21 or “Compound 22”.

Test results indicate that the compounds of the present invention arehighly active preemergent and/or postemergent herbicides and/or plantgrowth regulants. The compounds of the inention generally show highestactivity for postemergence weed control (i.e. applied after weedseedlings emerge from the soil) and preemergence weed control (i.e.applied before weed seedlings emerge from the soil). Many of them haveutility for broad-spectrum pre- and/or postemergence weed control inareas where complete control of all vegetation is desired such as aroundfuel storage tanks, industrial storage areas, parking lots, drive-intheaters, air fields, river banks, irrigation and other waterways,around billboards and highway and railroad structures. Many of thecompounds of this invention, by virtue of selective metabolism in cropsversus weeds, or by selective activity at the locus of physiologicalinhibition in crops and weeds, or by selective placement on or withinthe environment of a mixture of crops and weeds, are useful for theselective control of grass and broadleaf weeds within a crop/weedmixture. One skilled in the art will recognize that the preferredcombination of these selectivity factors within a compound or group ofcompounds can readily be determined by performing routine biologicaland/or biochemical assays. Compounds of this invention may showtolerance to important agronomic crops including, but is not limited to,alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize),sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato,perennial plantation crops including coffee, cocoa, oil palm, rubber,sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain,pineapple, hops, tea and forests such as eucalyptus and conifers (e.g.,loblolly pine), and turf species (e.g., Kentucky bluegrass, St.Augustine grass, Kentucky fescue and Bermuda grass). Compounds of thisinvention can be used in crops genetically transformed or bred toincorporate resistance to herbicides, express proteins toxic toinvertebrate pests (such as Bacillus thuringiensis toxin), and/orexpress other useful traits. Those skilled in the art will appreciatethat not all compounds are equally effective against all weeds.Alternatively, the subject compounds are useful to modify plant growth.

As the compounds of the invention have both preemergent and postemergentherbicidal activity, to control undesired vegetation by killing orinjuring the vegetation or reducing its growth, the compounds can beusefully applied by a variety of methods involving contacting aherbicidally effective amount of a compound of the invention, or acomposition comprising said compound and at least one of a surfactant, asolid diluent or a liquid diluent, to the foliage or other part of theundesired vegetation or to the environment of the undesired vegetationsuch as the soil or water in which the undesired vegetation is growingor which surrounds the seed or other propagule of the undesiredvegetation.

A herbicidally effective amount of the compounds of this invention isdetermined by a number of factors. These factors include: formulationselected, method of application, amount and type of vegetation present,growing conditions, etc. In general, a herbicidally effective amount ofcompounds of this invention is about 0.001 to 20 kg/ha with a preferredrange of about 0.004 to 1 kg/ha. One skilled in the art can easilydetermine the herbicidally effective amount necessary for the desiredlevel of weed control.

In one common embodiment, a compound of the invention is applied,typically in a formulated composition, to a locus comprising desiredvegetation (e.g., crops) and undesired vegetation (i.e. weeds), both ofwhich may be seeds, seedlings and/or larger plants, in contact with agrowth medium (e.g., soil). In this locus, a composition comprising acompound of the invention can be directly applied to a plant or a partthereof, particularly of the undesired vegetation, and/or to the growthmedium in contact with the plant.

Plant varieties and cultivars of the desired vegetation in the locustreated with a compound of the invention can be obtained by conventionalpropagation and breeding methods or by genetic engineering methods.Genetically modified plants (transgenic plants) are those in which aheterologous gene (transgene) has been stably integrated into theplant's genome. A transgene that is defined by its particular locationin the plant genome is called a transformation or transgenic event.

Genetically modified plant cultivars in the locus which can be treatedaccording to the invention include those that are resistant against oneor more biotic stresses (pests such as nematodes, insects, mites, fungi,etc.) or abiotic stresses (drought, cold temperature, soil salinity,etc.), or that contain other desirable characteristics. Plants can begenetically modified to exhibit traits of, for example, herbicidetolerance, insect-resistance, modified oil profiles or droughttolerance. Useful genetically modified plants containing single genetransformation events or combinations of transformation events arelisted in Exhibit C. Additional information for the geneticmodifications listed in Exhibit C can be obtained from publiclyavailable databases maintained, for example, by the U.S. Department ofAgriculture.

The following abbreviations, Ti through T37, are used in Exhibit C fortraits. A “−” means the entry is not available; “tol.” means “tolerance”and “res.” means resistance.

Trait Description T1 Glyphosate tol. T2 High lauric acid oil T3Glufosinate tol. T4 Phytate breakdown T5 Oxynil tol. T6 Disease res. T7Insect res. T9 Modified flower color T11 ALS Herbicide tol. T12 Dicambatol. T13 Anti-allergy T14 Salt tol. T15 Cold tol. T16 Imidazolinoneherb. tol. T17 Modified alpha-amylase T18 Pollination control T19 2,4-Dtol. T20 Increased lysine T21 Drought tol. T22 Delayedripening/senescence T23 Modified product quality T24 High cellulose T25Modified starch/carbohydrate T26 Insect & disease resist. T27 Hightryptophan T28 Erect leaves semidwarf T29 Semidwarf T30 Low iron tol.T31 Modified oil/fatty acid T32 HPPD tol. T33 High oil T34Aryloxyalkanoate tol. T35 Mesotrione tol. T36 Reduced nicotine T37Modified product

Exhibit C

Crop Event Name Event Code Trait(s) Gene(s) Alfalfa J101 MON-00101-8 T1cp4 epsps (aroA:CP4) Alfalfa J163 MON-ØØ163-7 T1 cp4 epsps (aroA:CP4)Canola* 23-18-17 (Event 18) CGN-89465-2 T2 te Canola* 23-198 (Event 23)CGN-89465-2 T2 te Canola* 61061 DP-Ø61Ø61-7 T1 gat4621 Canola* 73496DP-Ø73496-4 T1 gat4621 Canola* GT200 (RT200) MON-89249-2 T1 cp4 epsps(aroA:CP4); goxv247 Canola* GT73 (RT73) MON-ØØØ73-7 T1 cp4 epsps(aroA:CP4); goxv247 Canola* HCN10 (Topas 19/2) — T3 bar Canola* HCN28(T45) ACS-BNØØ8-2 T3 pat (syn) Canola* HCN92 (Topas 19/2) ACS-BNØØ7-1 T3bar Canola* MON88302 MON-883Ø2-9 T1 cp4 epsps (aroA:CP4) Canola* MPS961— T4 phyA Canola* MPS962 — T4 phyA Canola* MPS963 — T4 phyA Canola*MPS964 — T4 phyA Canola* MPS965 — T4 phyA Canola* MS1 (B91-4)ACS-BNØØ4-7 T3 bar Canola* MS8 ACS-BNØØ5-8 T3 bar Canola* OXY-235ACS-BNØ11-5 T5 bxn Canola* PHY14 — T3 bar Canola* PHY23 — T3 bar Canola*PHY35 — T3 bar Canola* PHY36 — T3 bar Canola* RF1 (B93-101) ACS-BNØØ1-4T3 bar Canola* RF2 (B94-2) ACS-BNØØ2-5 T3 bar Canola* RF3 ACS-BNØØ3-6 T3bar Bean EMBRAPA 5.1 EMB-PV051-1 T6 ac1 (sense and antisense) Brinjal #EE-1 — T7 cry1Ac Cotton 19-51a DD-Ø1951A-7 T11 S4-HrA Cotton 281-24-236DAS-24236-5 T3, T7 pat (syn); cry1F Cotton 3006-210-23 DAS-21Ø23-5 T3,T7 pat (syn); cry1Ac Cotton 31707 — T5, T7 bxn; cry1Ac Cotton 31803 —T5, T7 bxn; cry1Ac Cotton 31807 — T5, T7 bxn; cry1Ac Cotton 31808 — T5,T7 bxn; cry1Ac Cotton 42317 — T5, T7 bxn; cry1Ac Cotton BNLA-601 — T7cry1Ac Cotton BXN10211 BXN10211-9 T5 bxn; cry1Ac Cotton BXN10215BXN10215-4 T5 bxn; cry1Ac Cotton BXN10222 BXN10222-2 T5 bxn; cry1AcCotton BXN10224 BXN10224-4 T5 bxn; cry1Ac Cotton COT102 SYN-IR102-7 T7vip3A(a) Cotton COT67B SYN-IR67B-1 T7 cry1Ab Cotton COT202 — T7 vip3ACotton Event 1 — T7 cry1Ac Cotton GMF Cry1A GTL-GMF311-7 T7 cry1Ab-AcCotton GHB119 BCS-GH005-8 T7 cry2Ae Cotton GHB614 BCS-GH002-5 T1 2mepspsCotton GK12 — T7 cry1Ab-Ac Cotton LLCotton25 ACS-GH001-3 T3 bar CottonMLS 9124 — T7 cry1C Cotton MON1076 MON-89924-2 T7 cry1Ac Cotton MON1445MON-01445-2 T1 cp4 epsps (aroA:CP4) Cotton MON15985 MON-15985-7 T7cry1Ac; cry2Ab2 Cotton MON1698 MON-89383-1 T7 cp4 epsps (aroA:CP4)Cotton MON531 MON-00531-6 T7 cry1Ac Cotton MON757 MON-00757-7 T7 cry1AcCotton MON88913 MON-88913-8 T1 cp4 epsps (aroA:CP4) Cotton Nqwe Chi 6 Bt— T7 — Cotton SKG321 — T7 cry1A; CpTI Cotton T303-3 BCS-GH003-6 T3, T7cry1Ab; bar Cotton T304-40 BCS-GH004-7 T3, T7 cry1Ab; bar CottonCE43-67B — T7 cry1Ab Cotton CE46-02A — T7 cry1Ab Cotton CE44-69D — T7cry1Ab Cotton 1143-14A — T7 cry1Ab Cotton 1143-51B — T7 cry1Ab CottonT342-142 — T7 cry1Ab Cotton PV-GHGT07 (1445) — T1 cp4 epsps (aroA:CP4)Cotton EE-GH3 — T1 mepsps Cotton EE-GH5 — T7 cry1Ab Cotton MON88701MON-88701-3 T3, T12 Modified dmo; bar Cotton OsCr11 — T13 Modified Cry jFlax FP967 CDC-FL001-2 T11 als Lentil RH44 — T16 als Maize  3272SYN-E3272-5 T17 amy797E Maize  5307 SYN-05307-1 T7 ecry3.1Ab Maize 59122DAS-59122-7 T3, T7 cry34Ab1; cry35Ab1; pat Maize  676 PH-000676-7 T3,T18 pat; dam Maize  678 PH-000678-9 T3, T18 pat; dam Maize  680PH-000680-2 T3, T18 pat; dam Maize 98140 DP-098140-6 T1, T11 gat4621;zm-hra Maize Bt10 — T3, T7 cry1Ab; pat Maize Bt176 (176) SYN-EV176-9 T3,T7 cry1Ab; bar Maize BVLA430101 — T4 phyA2 Maize CBH-351 ACS-ZM004-3 T3,T7 cry9C; bar Maize DAS40278-9 DAS40278-9 T19 aad-1 Maize DBT418DKB-89614-9 T3, T7 cry1Ac; pinII; bar Maize DLL25 (B16) DKB-89790-5 T3bar Maize GA21 MON-00021-9 T1 mepsps Maize GG25 — T1 mepsps Maize GJ11 —T1 mepsps Maize Fl117 — T1 mepsps Maize GAT-ZM1 — T3 pat Maize LY038REN-00038-3 T20 cordapA Maize MIR162 SYN-IR162-4 T7 vip3Aa20 MaizeMIR604 SYN-IR604-5 T7 mcry3A Maize MON801 (MON80100) MON801 T1, T7cry1Ab; cp4 epsps (aroA:CP4); goxv247 Maize MON802 MON-80200-7 T1, T7cry1Ab; cp4 epsps (aroA:CP4); goxv247 Maize MON809 PH-MON-809-2 T1, T7cry1Ab; cp4 epsps (aroA:CP4); goxv247 Maize MON810 MON-00810-6 T1, T7cry1Ab; cp4 epsps (aroA:CP4); goxv247 Maize MON832 — T1 cp4 epsps(aroA:CP4); goxv247 Maize MON863 MON-00863-5 T7 cry3Bb1 Maize MON87427MON-87427-7 T1 cp4 epsps (aroA:CP4) Maize MON87460 MON-87460-4 T21 cspBMaize MON88017 MON-88017-3 T1, T7 cry3Bb1; cp4 epsps (aroA:CP4) MaizeMON89034 MON-89034-3 T7 cry2Ab2; cry1A.105 Maize MS3 ACS-ZM001-9 T3, T18bar; barnase Maize MS6 ACS-ZM005-4 T3, T18 bar; barnase Maize NK603MON-00603-6 T1 cp4 epsps (aroA:CP4) Maize T14 ACS-ZM002-1 T3 pat (syn)Maize T25 ACS-ZM003-2 T3 pat (syn) Maize TC1507 DAS-01507-1 T3, T7cry1Fa2; pat Maize TC6275 DAS-06275-8 T3, T7 mocry1F; bar Maize VIP1034— T3, T7 vip3A; pat Maize 43A47 DP-043A47-3 T3, T7 cry1F; cry34Ab1;cry35Ab1; pat Maize 40416 DP-040416-8 T3, T7 cry1F; cry34Ab1; cry35Ab1;pat Maize 32316 DP-032316-8 T3, T7 cry1F; cry34Ab1; cry35Ab1; pat Maize 4114 DP-004114-3 T3, T7 cry1F; cry34Ab1; cry35Ab1; pat Melon Melon A —T22 sam-k Melon Melon B — T22 sam-k Papaya 55-1 CUH-CP551-8 T6 prsv cpPapaya 63-1 CUH-CP631-7 T6 prsv cp Papaya Huanong No. 1 — T6 prsv repPapaya X17-2 UFL-X17CP-6 T6 prsv cp Plum C-5 ARS-PLMC5-6 T6 ppv cpCanola** ZSR500 — T1 cp4 epsps (aroA:CP4); goxv247 Canola** ZSR502 — T1cp4 epsps (aroA:CP4); goxv247 Canola** ZSR503 — T1 cp4 epsps (aroA:CP4);goxv247 Rice 7Crp#242-95-7 — T13 7crp Rice 7Crp#10 — T13 7crp Rice GMShanyou 63 — T7 cry1Ab; cry1Ac Rice Huahui-1/TT51-1 — T7 cry1Ab; cry1AcRice LLRICE06 ACS-OS001-4 T3 bar Rice LLRICE601 BCS-OS003-7 T3 bar RiceLLRICE62 ACS-OS002-5 T3 bar Rice Tarom molaii + cry1Ab — T7 cry1Ab(truncated) Rice GAT-OS2 — T3 bar Rice GAT-OS3 — T3 bar Rice PE-7 — T7Cry1Ac Rice 7Crp#10 — T13 7crp Rice KPD627-8 — T27 OASA1D Rice KPD722-4— T27 OASA1D Rice KA317 — T27 OASA1D Rice HW5 — T27 OASA1D Rice HW1 —T27 OASA1D Rice B-4-1-18 — T28 Δ OsBRI1 Rice G-3-3-22 — T29 OSGA2ox1Rice AD77 — T6 DEF Rice AD51 — T6 DEF Rice AD48 — T6 DEF Rice AD41 — T6DEF Rice 13pNasNa800725atAprt1 — T30 HvNAS1; HvNAAT-A; APRT Rice13pAprt1 — T30 APRT Rice gHvNAS1-gHvNAAT-1 — T30 HvNAS1; HvNAAT-A;HvNAAT-B Rice gHvIDS3-1 — T30 HvIDS3 Rice gHvNAAT1 — T30 HvNAAT-A;HvNAAT-B Rice gHvNAS1-1 — T30 HvNAS1 Rice NIA-OS006-4 — T6 WRKY45 RiceNIA-OS005-3 — T6 WRKY45 Rice NIA-OS004-2 — T6 WRKY45 Rice NIA-OS003-1 —T6 WRKY45 Rice NIA-OS002-9 — T6 WRKY45 Rice NIA-OS001-8 — T6 WRKY45 RiceOsCr11 — T13 Modified Cry j Rice 17053 — T1 cp4 epsps (aroA:CP4) Rice17314 — T1 cp4 epsps (aroA:CP4) Rose WKS82/130-4-1 IFD-52401-4 T9 5AT;bp40 (f3′5′h) Rose WKS92/130-9-1 IFD-52901-9 T9 5AT; bp40 (f3′5′h)Soybean 260-05 (G94-1, G94-19, — T9 gm-fad2-1 (silencing locus) G168)Soybean A2704-12 ACS-GM005-3 T3 pat Soybean A2704-21 ACS-GM004-2 T3 patSoybean A5547-127 ACS-GM006-4 T3 pat Soybean A5547-35 ACS-GM008-6 T3 patSoybean CV127 BPS-CV127-9 T16 csr1-2 Soybean DAS68416-4 DAS68416-4 T3pat Soybean DP305423 DP-305423-1 T11, T31 gm-fad2-1 (silencing locus);gm-hra Soybean DP356043 DP-356043-5 T1, T31 gm-fad2-1 (silencing locus);gat4601 Soybean FG72 MST-FG072-3 T32, T1 2mepsps; hppdPF W336 SoybeanGTS 40-3-2 (40-3-2) MON-04032-6 T1 cp4 epsps (aroA:CP4) Soybean GU262ACS-GM003-1 T3 pat Soybean MON87701 MON-87701-2 T7 cry1Ac SoybeanMON87705 MON-87705-6 T1, T31 fatb1-A (sense & antisense); fad2- 1A(sense & antisense); cp4 epsps (aroA:CP4) Soybean MON87708 MON-87708-9T1, T12 dmo; cp4 epsps (aroA:CP4) Soybean MON87769 MON-87769-7 T1, T31Pj.D6D; Nc.Fad3; cp4 epsps (aroA:CP4) Soybean MON89788 MON-89788-1 T1cp4 epsps (aroA:CP4) Soybean W62 ACS-GM002-9 T3 bar Soybean W98ACS-GM001-8 T3 bar Soybean MON87754 MON-87754-1 T33 dgat2A SoybeanDAS21606 DAS-21606 T34, T3 Modified aad-12; pat Soybean DAS44406DAS-44406-6 T1, T3, T34 Modified aad-12; 2mepsps; pat Soybean SYHT04RSYN-0004R-8 T35 Modified avhppd Soybean 9582.814.19.1 — T3, T7 cry1Ac,cry1F, PAT Squash CZW3 SEM-ØCZW3-2 T6 cmv cp, zymv cp, wmv cp SquashZW20 SEM-0ZW20-7 T6 zymv cp, wmv cp Sugar Beet GTSB77 (T9100152)SY-GTSB77-8 T1 cp4 epsps (aroA:CP4); goxv247 Sugar Beet H7-1 KM-000H71-4T1 cp4 epsps (aroA:CP4) Sugar Beet T120-7 ACS-BV001-3 T3 pat Sugar BeetT227-1 — T1 cp4 epsps (aroA:CP4) Sugarcane NXI-1T — T21 EcbetA SunflowerX81359 — T16 als Pepper PK-SP01 — T6 cmv cp Tobacco C/F/93/08-02 — T5bxn Tobacco Vector 21-41 — T36 NtQPT1 (antisense) Sunflower X81359 — T16als Wheat MON71800 MON-718ØØ-3 T1 cp4 epsps (aroA:CP4) *Argentine(Brassica napus), **Polish (B. rapa), # Eggplant

Although most typically, compounds of the invention are used to controlundesired vegetation, contact of desired vegetation in the treated locuswith compounds of the invention may result in super-additive orsynergistic effects with genetic traits in the desired vegetation,including traits incorporated through genetic modification. For example,resistance to phytophagous insect pests or plant diseases, tolerance tobiotic/abiotic stresses or storage stability may be greater thanexpected from the genetic traits in the desired vegetation.

Compounds of this invention can also be mixed with one or more otherbiologically active compounds or agents including herbicides, herbicidesafeners, fungicides, insecticides, nematocides, bactericides,acaricides, growth regulators such as insect molting inhibitors androoting stimulants, chemosterilants, semiochemicals, repellents,attractants, pheromones, feeding stimulants, plant nutrients, otherbiologically active compounds or entomopathogenic bacteria, virus orfungi to form a multi-component pesticide giving an even broaderspectrum of agricultural protection. Mixtures of the compounds of theinvention with other herbicides can broaden the spectrum of activityagainst additional weed species, and suppress the proliferation of anyresistant biotypes. Thus the present invention also pertains to acomposition comprising a compound of Formula 1 (in a herbicidallyeffective amount) and at least one additional biologically activecompound or agent (in a biologically effective amount) and can furthercomprise at least one of a surfactant, a solid diluent or a liquiddiluent. The other biologically active compounds or agents can beformulated in compositions comprising at least one of a surfactant,solid or liquid diluent. For mixtures of the present invention, one ormore other biologically active compounds or agents can be formulatedtogether with a compound of Formula 1, to form a premix, or one or moreother biologically active compounds or agents can be formulatedseparately from the compound of Formula 1, and the formulations combinedtogether before application (e.g., in a spray tank) or, alternatively,applied in succession.

A mixture of one or more of the following herbicides with a compound ofthis invention may be particularly useful for weed control: acetochlor,acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal),alachlor, alloxydim, ametryn, amicarbazone, amidosulfuron,aminocyclopyrachlor and its esters (e.g., methyl, ethyl) and salts(e.g., sodium, potassium), aminopyralid, amitrole, ammonium sulfamate,anilofos, asulam, atrazine, azimsulfuron, beflubutamid, benazolin,benazolin-ethyl, bencarbazone, benfluralin, benfuresate,bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap,bicyclopyrone, bifenox, bilanafos, bispyribac and its sodium salt,bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil octanoate,butachlor, butafenacil, butamifos, butralin, butroxydim, butylate,cafenstrole, carbetamide, carfentrazone-ethyl, catechin, chlomethoxyfen,chloramben, chlorbromuron, chlorflurenol-methyl, chloridazon,chlorimuron-ethyl, chlorotoluron, chlorpropham, chlorsulfuron,chlorthal-dimethyl, chlorthiamid, cinidon-ethyl, cinmethylin,cinosulfuron, clacyfos, clefoxydim, clethodim, clodinafop-propargyl,clomazone, clomeprop, clopyralid, clopyralid-olamine,cloransulam-methyl, cumyluron, cyanazine, cycloate, cyclopyrimorate,cyclosulfamuron, cycloxydim, cyhalofop-butyl, 2,4-D and its butotyl,butyl, isoctyl and isopropyl esters and its dimethylammonium, diolamineand trolamine salts, daimuron, dalapon, dalapon-sodium, dazomet, 2,4-DBand its dimethylammonium, potassium and sodium salts, desmedipham,desmetryn, dicamba and its diglycolammonium, dimethylammonium, potassiumand sodium salts, dichlobenil, dichlorprop, diclofop-methyl, diclosulam,difenzoquat metilsulfate, diflufenican, diflufenzopyr, dimefuron,dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P,dimethipin, dimethylarsinic acid and its sodium salt, dinitramine,dinoterb, diphenamid, diquat dibromide, dithiopyr, diuron, DNOC,endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl,ethiozin, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid,fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione,fentrazamide, fenuron, fenuron-TCA, flamprop-methyl,flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam,fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone,flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl,flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron,fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl and its sodiumsalt, flurenol, flurenol-butyl, fluridone, flurochloridone, fluroxypyr,flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron,fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-P,glyphosate and its salts such as ammonium, isopropylammonium, potassium,sodium (including sesquisodium) and trimesium (alternatively namedsulfosate), halauxifen, halauxifen-methyl, halosulfuron-methyl,haloxyfop-etotyl, haloxyfop-methyl, hexazinone, hydantocidin,imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin,imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron,indanofan, indaziflam, iofensulfuron, iodosulfuron-methyl, ioxynil,ioxynil octanoate, ioxynil-sodium, ipfencarbazone, isoproturon, isouron,isoxaben, isoxaflutole, isoxachlortole, lactofen, lenacil, linuron,maleic hydrazide, MCPA and its salts (e.g., MCPA-dimethylammonium,MCPA-potassium and MCPA-sodium, esters (e.g., MCPA-2-ethylhexyl,MCPA-butotyl) and thioesters (e.g., MCPA-thioethyl), MCPB and its salts(e.g., MCPB-sodium) and esters (e.g., MCPB-ethyl), mecoprop, mecoprop-P,mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metam-sodium,metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron,methylarsonic acid and its calcium, monoammonium, monosodium anddisodium salts, methyldymron, metobenzuron, metobromuron, metolachlor,S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl,molinate, monolinuron, naproanilide, napropamide, napropamide-M,naptalam, neburon, nicosulfuron, norflurazon, orbencarb,orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,oxaziclomefone, oxyfluorfen, paraquat dichloride, pebulate, pelargonicacid, pendimethalin, penoxsulam, pentanochlor, pentoxazone, perfluidone,pethoxamid, pethoxyamid, phenmedipham, picloram, picloram-potassium,picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl,prodiamine, profoxydim, prometon, prometryn, propachlor, propanil,propaquizafop, propazine, propham, propisochlor, propoxycarbazone,propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil,pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazoxyfen,pyrazosulfuron-ethyl, pyribenzoxim, pyributicarb, pyridate, pyriftalid,pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium,pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine,quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron,saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione,sulfentrazone, sulfometuron-methyl, sulfosulfuron, 2,3,6-TBA, TCA,TCA-sodium, tebutam, tebuthiuron, tefuryltrione, tembotrione,tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn,thenylchlor, thiazopyr, thiencarbazone, thifensulfuron-methyl,thiobencarb, tiafenacil, tiocarbazil, tolpyralate, topramezone,tralkoxydim, tri-allate, triafamone, triasulfuron, triaziflam,tribenuron-methyl, triclopyr, triclopyr-butotyl,triclopyr-triethylammonium, tridiphane, trietazine, trifloxysulfuron,trifludimoxazin, trifluralin, triflusulfuron-methyl, tritosulfuron,vernolate,3-(2-chloro-3,6-difluorophenyl)-4-hydroxy-1-methyl-1,5-naphthyridin-2(1H)-one,5-chloro-3-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-1-(4-methoxyphenyl)-2(1H)-quinoxalinone,2-chloro-N-(1-methyl-1H-tetrazol-5-yl)-6-(trifluoromethyl)-3-pyridinecarboxamide,7-(3,5-dichloro-4-pyridinyl)-5-(2,2-difluoroethyl)-8-hydroxypyrido[2,3-b]pyrazin-6(5H)-one),4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone), 5-[[(2,6-difluorophenyl)methoxy]methyl]-4,5-dihydro-5-methyl-3-(3-methyl-2-thienyl)isoxazole (previouslymethioxolin),4-(4-fluorophenyl)-6-[(2-hydroxy-6-oxo-1-cyclohexen-1-yl)carbonyl]-2-methyl-1,2,4-triazine-3,5(2H,4H)-dione,methyl4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoro-2-pyridinecarboxylate,2-methyl-3-(methylsulfonyl)-N-(1-methyl-1H-tetrazol-5-yl)-4-(trifluoromethyl)benzamide and2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfinyl)-4-(trifluoromethyl)benzamide. Other herbicides also includebioherbicides such as Alternaria destruens Simmons, Colletotrichumgloeosporiodes (Penz.) Penz. & Sacc., Drechsiera monoceras (MTB-951),Myrothecium verrucaria (Albertini & Schweinitz) Ditmar: Fries,Phytophthora palmivora (Butl.) Butl. and Puccinia thlaspeos Schub.

Compounds of this invention can also be used in combination with plantgrowth regulators such as aviglycine, N-(phenylmethyl)-1H-purin-6-amine,epocholeone, gibberellic acid, gibberellin A₄ and A₇, harpin protein,mepiquat chloride, prohexadione calcium, prohydrojasmon, sodiumnitrophenolate and trinexapac-methyl, and plant growth modifyingorganisms such as Bacillus cereus strain BP01.

General references for agricultural protectants (i.e. herbicides,herbicide safeners, insecticides, fungicides, nematocides, acaricidesand biological agents) include The Pesticide Manual, 13th Edition, C. D.S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U. K.,2003 and The BioPesticide Manual, 2nd Edition, L. G. Copping, Ed.,British Crop Protection Council, Farnham, Surrey, U. K., 2001.

For embodiments where one or more of these various mixing partners areused, the mixing partners are typically used in the amounts similar toamounts customary when the mixture partners are used alone. Moreparticularly in mixtures, active ingredients are often applied at anapplication rate between one-half and the full application ratespecified on product labels for use of active ingredient alone. Theseamounts are listed in references such as The Pesticide Manual and TheBioPesticide Manual. The weight ratio of these various mixing partners(in total) to the compound of Formula 1 is typically between about1:3000 and about 3000:1. Of note are weight ratios between about 1:300and about 300:1 (for example ratios between about 1:30 and about 30:1).One skilled in the art can easily determine through simpleexperimentation the biologically effective amounts of active ingredientsnecessary for the desired spectrum of biological activity. It will beevident that including these additional components may expand thespectrum of weeds controlled beyond the spectrum controlled by thecompound of Formula 1 alone.

In certain instances, combinations of a compound of this invention withother biologically active (particularly herbicidal) compounds or agents(i.e. active ingredients) can result in a greater-than-additive (i.e.synergistic) effect on weeds and/or a less-than-additive effect (i.e.safening) on crops or other desirable plants. Reducing the quantity ofactive ingredients released in the environment while ensuring effectivepest control is always desirable. Ability to use greater amounts ofactive ingredients to provide more effective weed control withoutexcessive crop injury is also desirable. When synergism of herbicidalactive ingredients occurs on weeds at application rates givingagronomically satisfactory levels of weed control, such combinations canbe advantageous for reducing crop production cost and decreasingenvironmental load. When safening of herbicidal active ingredientsoccurs on crops, such combinations can be advantageous for increasingcrop protection by reducing weed competition.

Of note is a combination of a compound of the invention with at leastone other herbicidal active ingredient. Of particular note is such acombination where the other herbicidal active ingredient has differentsite of action from the compound of the invention. In certain instances,a combination with at least one other herbicidal active ingredienthaving a similar spectrum of control but a different site of action willbe particularly advantageous for resistance management. Thus, acomposition of the present invention can further comprise (in aherbicidally effective amount) at least one additional herbicidal activeingredient having a similar spectrum of control but a different site ofaction.

Compounds of this invention can also be used in combination withherbicide safeners such as allidochlor, benoxacor, cloquintocet-mexyl,cumyluron, cyometrinil, cyprosulfonamide, daimuron, dichlormid,dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim,flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl,mephenate, methoxyphenone naphthalic anhydride (1,8-naphthalicanhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide,N-(aminocarbonyl)-2-fluorobenzenesulfonamide,1-bromo-4-[(chloromethyl)sulfonyl]benzene (BCS),4-(dichloroacetyl)-1-oxa-4-azospiro[4.5]decane (MON 4660),2-(dichloromethyl)-2-methyl-1,3-dioxolane (MG 191), ethyl1,6-dihydro-1-(2-methoxyphenyl)-6-oxo-2-phenyl-5-pyrimidinecarboxylate,2-hydroxy-N,N-dimethyl-6-(trifluoromethyl)pyridine-3-carboxamide, and3-oxo-1-cyclohexen-1-yl1-(3,4-dimethylphenyl)-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxylate,2,2-dichloro-1-(2,2,5-trimethyl-3-oxazolidinyl)-ethanone and2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]-benzamideto increase safety to certain crops. Antidotally effective amounts ofthe herbicide safeners can be applied at the same time as the compoundsof this invention, or applied as seed treatments. Therefore an aspect ofthe present invention relates to a herbicidal mixture comprising acompound of this invention and an antidotally effective amount of aherbicide safener. Seed treatment is particularly useful for selectiveweed control, because it physically restricts antidoting to the cropplants. Therefore a particularly useful embodiment of the presentinvention is a method for selectively controlling the growth ofundesired vegetation in a crop comprising contacting the locus of thecrop with a herbicidally effective amount of a compound of thisinvention wherein seed from which the crop is grown is treated with anantidotally effective amount of safener. Antidotally effective amountsof safeners can be easily determined by one skilled in the art throughsimple experimentation.

Compounds of the invention cans also be mixed with: (1) polynucleotidesincluding but not limited to DNA, RNA, and/or chemically modifiednucleotides influencing the amount of a particular target through downregulation, interference, suppression or silencing of the geneticallyderived transcript that render a herbicidal effect; or (2)polynucleotides including but not limited to DNA, RNA, and/or chemicallymodified nucleotides influencing the amount of a particular targetthrough down regulation, interference, suppression or silencing of thegenetically derived transcript that render a safening effect.

Of note is a composition comprising a compound of the invention (in aherbicidally effective amount), at least one additional activeingredient selected from the group consisting of other herbicides andherbicide safeners (in an effective amount), and at least one componentselected from the group consisting of surfactants, solid diluents andliquid diluents.

Table A1 lists specific combinations of a Component (a) with Component(b) illustrative of the mixtures, compositions and methods of thepresent invention. Compound 6 in the Component (a) column is identifiedin Index Table A. The second column of Table A1 lists the specificComponent (b) compound (e.g., “2,4-D” in the first line). The third,fourth and fifth columns of Table A1 lists ranges of weight ratios forrates at which the Component (a) compound is typically applied to afield-grown crop relative to Component (b) (i.e. (a):(b)). Thus, forexample, the first line of Table A1 specifically discloses thecombination of Component (a) (i.e. Compound 6 in Index Table A) with2,4-D is typically applied in a weight ratio between 1:192-6:1. Theremaining lines of Table A1 are to be construed similarly.

TABLE A1 Component (a) Typical More Typical Most Typical (Compound #)Component (b) Weight Ratio Weight Ratio Weight Ratio 6 2,4-D 1:192-6:11:64-2:1 1:24-1:3 6 Acetochlor 1:768-2:1 1:256-1:2   1:96-1:11 6Acifluorfen  1:96-12:1 1:32-4:1 1:12-1:2 6 Aclonifen 1:857-2:11:285-1:3  1:107-1:12 6 Alachlor 1:768-2:1 1:256-1:2   1:96-1:11 6Ametryn 1:384-3:1 1:128-1:1  1:48-1:6 6 Amicarbazone 1:192-6:1 1:64-2:11:24-1:3 6 Amidosulfuron   1:6-168:1  1:2-56:1  1:1-11:1 6Aminocyclopyrachlor  1:48-24:1 1:16-8:1  1:6-2:1 6 Aminopyralid 1:20-56:1  1:6-19:1  1:2-4:1 6 Amitrole 1:768-2:1 1:256-1:2   1:96-1:116 Anilofos  1:96-12:1 1:32-4:1 1:12-1:2 6 Asulam 1:960-2:1 1:320-1:3 1:120-1:14 6 Atrazine 1:192-6:1 1:64-2:1 1:24-1:3 6 Azimsulfuron  1:6-168:1  1:2-56:1  1:1-11:1 6 Beflubutamid 1:342-4:1 1:114-2:1 1:42-1:5 6 Benfuresate 1:617-2:1 1:205-1:2  1:77-1:9 6Bensulfuron-methyl  1:25-45:1  1:8-15:1  1:3-3:1 6 Bentazone 1:192-6:11:64-2:1 1:24-1:3 6 Benzobicyclon  1:85-14:1 1:28-5:1 1:10-1:2 6Benzofenap 1:257-5:1 1:85-2:1 1:32-1:4 6 Bicyclopyrone  1:42-27:11:14-9:1  1:5-2:1 6 Bifenox 1:257-5:1 1:85-2:1 1:32-1:4 6Bispyribac-sodium   1:10-112:1  1:3-38:1  1:1-7:1 6 Bromacil 1:384-3:11:128-1:1  1:48-1:6 6 Bromobutide 1:384-3:1 1:128-1:1  1:48-1:6 6Bromoxynil  1:96-12:1 1:32-4:1 1:12-1:2 6 Butachlor 1:768-2:1 1:256-1:2  1:96-1:11 6 Butafenacil  1:42-27:1 1:14-9:1  1:5-2:1 6 Butylate1:1542-1:2  1:514-1:5  1:192-1:22 6 Cafenstrole 1:192-6:1 1:64-2:11:24-1:3 6 Carfentrazone-ethyl 1:128-9:1 1:42-3:1 1:16-1:2 6Chlorimuron-ethyl   1:8-135:1  1:2-45:1  1:1-9:1 6 Chlorotoluron1:768-2:1 1:256-1:2   1:96-1:11 6 Chlorsulfuron   1:6-168:1  1:2-56:1 1:1-11:1 6 Cinosulfuron  1:17-68:1  1:5-23:1  1:2-5:1 6 Cinidon-ethyl1:384-3:1 1:128-1:1  1:48-1:6 6 Cinmethylin  1:34-34:1  1:11-12:1 1:4-3:1 6 Clacyfos  1:34-34:1  1:11-12:1  1:4-3:1 6 Clethodim 1:48-24:1 1:16-8:1  1:6-2:1 6 Clodinafop-propargyl  1:20-56:1  1:6-19:1 1:2-4:1 6 Clomazone 1:384-3:1 1:128-1:1  1:48-1:6 6 Clomeprop 1:171-7:11:57-3:1 1:21-1:3 6 Clopyralid 1:192-6:1 1:64-2:1 1:24-1:3 6Cloransulam-methyl  1:12-96:1  1:4-32:1  1:1-6:1 6 Cumyluron 1:384-3:11:128-1:1  1:48-1:6 6 Cyanazine 1:384-3:1 1:128-1:1  1:48-1:6 6Cyclopyrimorate  1:17-68:1  1:5-23:1  1:2-5:1 6 Cyclosulfamuron 1:17-68:1  1:5-23:1  1:2-5:1 6 Cycloxydim  1:96-12:1 1:32-4:1 1:12-1:26 Cyhalofop  1:25-45:1  1:8-15:1  1:3-3:1 6 Daimuron 1:192-6:1 1:64-2:11:24-1:3 6 Desmedipham 1:322-4:1 1:107-2:1  1:40-1:5 6 Dicamba 1:192-6:11:64-2:1 1:24-1:3 6 Dichlobenil 1:1371-1:2  1:457-1:4  1:171-1:20 6Dichlorprop 1:925-2:1 1:308-1:3  1:115-1:13 6 Diclofop-methyl 1:384-3:11:128-1:1  1:48-1:6 6 Diclosulam   1:10-112:1  1:3-38:1  1:1-7:1 6Difenzoquat 1:288-4:1 1:96-2:1 1:36-1:4 6 Diflufenican 1:857-2:11:285-1:3  1:107-1:12 6 Diflufenzopyr  1:12-96:1  1:4-32:1  1:1-6:1 6Dimethachlor 1:768-2:1 1:256-1:2   1:96-1:11 6 Dimethametryn 1:192-6:11:64-2:1 1:24-1:3 6 Dimethenamid-P 1:384-3:1 1:128-1:1  1:48-1:6 6Dithiopyr 1:192-6:1 1:64-2:1 1:24-1:3 6 Diuron 1:384-3:1 1:128-1:1 1:48-1:6 6 EPTC 1:768-2:1 1:256-1:2   1:96-1:11 6 Esprocarb 1:1371-1:2 1:457-1:4  1:171-1:20 6 Ethalfluralin 1:384-3:1 1:128-1:1  1:48-1:6 6Ethametsulfuron-methyl  1:17-68:1  1:5-23:1  1:2-5:1 6 Ethoxyfen  1:8-135:1  1:2-45:1  1:1-9:1 6 Ethoxysulfuron  1:20-56:1  1:6-19:1 1:2-4:1 6 Etobenzanid 1:257-5:1 1:85-2:1 1:32-1:4 6 Fenoxaprop-ethyl 1:120-10:1 1:40-4:1 1:15-1:2 6 Fenoxasulfone  1:85-14:1 1:28-5:11:10-1:2 6 Fenquinotrione  1:17-68:1  1:5-23:1  1:2-5:1 6 Fentrazamide 1:17-68:1  1:5-23:1  1:2-5:1 6 Flazasulfuron  1:17-68:1  1:5-23:1 1:2-5:1 6 Florasulam   1:2-420:1   1:1-140:1  2:1-27:1 6Fluazifop-butyl 1:192-6:1 1:64-2:1 1:24-1:3 6 Flucarbazone   1:8-135:1 1:2-45:1  1:1-9:1 6 Flucetosulfuron   1:8-135:1  1:2-45:1  1:1-9:1 6Flufenacet 1:257-5:1 1:85-2:1 1:32-1:4 6 Flumetsulam  1:24-48:1 1:8-16:1  1:3-3:1 6 Flumiclorac-pentyl   1:10-112:1  1:3-38:1  1:1-7:16 Flumioxazin  1:25-45:1  1:8-15:1  1:3-3:1 6 Fluometuron 1:384-3:11:128-1:1  1:48-1:6 6 Flupyrsulfuron-methyl   1:3-336:1   1:1-112:1 2:1-21:1 6 Fluridone 1:384-3:1 1:128-1:1  1:48-1:6 6 Fluroxypyr 1:96-12:1 1:32-4:1 1:12-1:2 6 Flurtamone 1:857-2:1 1:285-1:3 1:107-1:12 6 Fluthiacet-methyl  1:48-42:1  1:16-14:1  1:3-3:1 6Fomesafen  1:96-12:1 1:32-4:1 1:12-1:2 6 Foramsulfuron  1:13-84:1 1:4-28:1  1:1-6:1 6 Glufosinate 1:288-4:1 1:96-2:1 1:36-1:4 6Glyphosate 1:288-4:1 1:96-2:1 1:36-1:4 6 Halauxifen  1:20-56:1  1:6-19:1 1:2-4:1 6 Halauxifen-methyl  1:20-56:1  1:6-19:1  1:2-4:1 6Halosulfuron-methyl  1:17-68:1  1:5-23:1  1:2-5:1 6 Haloxyfop-methyl 1:34-34:1  1:11-12:1  1:4-3:1 6 Hexazinone 1:192-6:1 1:64-2:1 1:24-1:36 Imazamox  1:13-84:1  1:4-28:1  1:1-6:1 6 Imazapic  1:20-56:1  1:6-19:1 1:2-4:1 6 Imazapyr  1:85-14:1 1:28-5:1 1:10-1:2 6 Imazaquin  1:34-34:1 1:11-12:1  1:4-3:1 6 Imazethabenz-methyl 1:171-7:1 1:57-3:1 1:21-1:3 6Imazethapyr  1:24-48:1  1:8-16:1  1:3-3:1 6 Imazosulfuron  1:27-42:1 1:9-14:1  1:3-3:1 6 Indanofan 1:342-4:1 1:114-2:1  1:42-1:5 6Indaziflam  1:25-45:1  1:8-15:1  1:3-3:1 6 Iodosulfuron-methyl  1:3-336:1   1:1-112:1  2:1-21:1 6 Ioxynil 1:192-6:1 1:64-2:1 1:24-1:36 Ipfencarbazone  1:85-14:1 1:28-5:1 1:10-1:2 6 Isoproturon 1:384-3:11:128-1:1  1:48-1:6 6 Isoxaben 1:288-4:1 1:96-2:1 1:36-1:4 6Isoxaflutole  1:60-20:1 1:20-7:1  1:7-2:1 6 Lactofen  1:42-27:1 1:14-9:1 1:5-2:1 6 Lenacil 1:384-3:1 1:128-1:1  1:48-1:6 6 Linuron 1:384-3:11:128-1:1  1:48-1:6 6 MCPA 1:192-6:1 1:64-2:1 1:24-1:3 6 MCPB 1:288-4:11:96-2:1 1:36-1:4 6 Mecoprop 1:768-2:1 1:256-1:2   1:96-1:11 6 Mefenacet1:384-3:1 1:128-1:1  1:48-1:6 6 Mefluidide 1:192-6:1 1:64-2:1 1:24-1:3 6Mesosulfuron-methyl   1:5-224:1  1:1-75:1  1:1-14:1 6 Mesotrione 1:42-27:1 1:14-9:1  1:5-2:1 6 Metamifop  1:42-27:1 1:14-9:1  1:5-2:1 6Metazachlor 1:384-3:1 1:128-1:1  1:48-1:6 6 Metazosulfuron  1:25-45:1 1:8-15:1  1:3-3:1 6 Methabenzthiazuron 1:768-2:1 1:256-1:2   1:96-1:116 Metolachlor 1:768-2:1 1:256-1:2   1:96-1:11 6 Metosulam   1:8-135:1 1:2-45:1  1:1-9:1 6 Metribuzin 1:192-6:1 1:64-2:1 1:24-1:3 6Metsulfuron-methyl   1:2-560:1   1:1-187:1  3:1-35:1 6 Molinate1:1028-2:1  1:342-1:3  1:128-1:15 6 Napropamide 1:384-3:1 1:128-1:1 1:48-1:6 6 Napropamide-M 1:192-6:1 1:64-2:1 1:24-1:3 6 Naptalam1:192-6:1 1:64-2:1 1:24-1:3 6 Nicosulfuron  1:12-96:1  1:4-32:1  1:1-6:16 Norflurazon 1:1152-1:1  1:384-1:3  1:144-1:16 6 Orbencarb 1:1371-1:2 1:457-1:4  1:171-1:20 6 Orthosulfamuron  1:20-56:1  1:6-19:1  1:2-4:1 6Oryzalin 1:514-3:1 1:171-1:2  1:64-1:8 6 Oxadiargyl 1:384-3:1 1:128-1:1 1:48-1:6 6 Oxadiazon 1:548-3:1 1:182-1:2  1:68-1:8 6 Oxasulfuron 1:27-42:1  1:9-14:1  1:3-3:1 6 Oxaziclomefone  1:42-27:1 1:14-9:1 1:5-2:1 6 Oxyfluorfen 1:384-3:1 1:128-1:1  1:48-1:6 6 Paraquat1:192-6:1 1:64-2:1 1:24-1:3 6 Pendimethalin 1:384-3:1 1:128-1:1 1:48-1:6 6 Penoxsulam   1:10-112:1  1:3-38:1  1:1-7:1 6 Penthoxamid1:384-3:1 1:128-1:1  1:48-1:6 6 Pentoxazone  1:102-12:1 1:34-4:11:12-1:2 6 Phenmedipham  1:102-12:1 1:34-4:1 1:12-1:2 6 Picloram 1:96-12:1 1:32-4:1 1:12-1:2 6 Picolinafen  1:34-34:1  1:11-12:1 1:4-3:1 6 Pinoxaden  1:25-45:1  1:8-15:1  1:3-3:1 6 Pretilachlor1:192-6:1 1:64-2:1 1:24-1:3 6 Primisulfuron-methyl   1:8-135:1  1:2-45:1 1:1-9:1 6 Prodiamine 1:384-3:1 1:128-1:1  1:48-1:6 6 Profoxydim 1:42-27:1 1:14-9:1  1:5-2:1 6 Prometryn 1:384-3:1 1:128-1:1  1:48-1:6 6Propachlor 1:1152-1:1  1:384-1:3  1:144-1:16 6 Propanil 1:384-3:11:128-1:1  1:48-1:6 6 Propaquizafop  1:48-24:1 1:16-8:1  1:6-2:1 6Propoxycarbazone  1:17-68:1  1:5-23:1  1:2-5:1 6 Propyrisulfuron 1:17-68:1  1:5-23:1  1:2-5:1 6 Propyzamide 1:384-3:1 1:128-1:1 1:48-1:6 6 Prosulfocarb 1:1200-1:2  1:400-1:4  1:150-1:17 6 Prosulfuron  1:6-168:1  1:2-56:1  1:1-11:1 6 Pyraclonil  1:42-27:1 1:14-9:1 1:5-2:1 6 Pyraflufen-ethyl   1:5-224:1  1:1-75:1  1:1-14:1 6Pyrasulfotole  1:13-84:1  1:4-28:1  1:1-6:1 6 Pyrazolynate 1:857-2:11:285-1:3  1:107-1:12 6 Pyrazosulfuron-ethyl   1:10-112:1  1:3-38:1 1:1-7:1 6 Pyrazoxyfen   1:5-224:1  1:1-75:1  1:1-14:1 6 Pyribenzoxim  1:10-112:1  1:3-38:1  1:1-7:1 6 Pyributicarb 1:384-3:1 1:128-1:1 1:48-1:6 6 Pyridate 1:288-4:1 1:96-2:1 1:36-1:4 6 Pyriftalid  1:10-112:1  1:3-38:1  1:1-7:1 6 Pyriminobac-methyl  1:20-56:1 1:6-19:1  1:2-4:1 6 Pyrimisulfan  1:17-68:1  1:5-23:1  1:2-5:1 6Pyrithiobac  1:24-48:1  1:8-16:1  1:3-3:1 6 Pyroxasulfone  1:85-14:11:28-5:1 1:10-1:2 6 Pyroxsulam   1:5-224:1  1:1-75:1  1:1-14:1 6Quinclorac 1:192-6:1 1:64-2:1 1:24-1:3 6 Quizalofop-ethyl  1:42-27:11:14-9:1  1:5-2:1 6 Rimsulfuron  1:13-84:1  1:4-28:1  1:1-6:1 6Saflufenacil  1:25-45:1  1:8-15:1  1:3-3:1 6 Sethoxydim  1:96-12:11:32-4:1 1:12-1:2 6 Simazine 1:384-3:1 1:128-1:1  1:48-1:6 6 Sulcotrione 1:120-10:1 1:40-4:1 1:15-1:2 6 Sulfentrazone 1:147-8:1 1:49-3:11:18-1:3 6 Sulfometuron-methyl  1:34-34:1  1:11-12:1  1:4-3:1 6Sulfosulfuron   1:8-135:1  1:2-45:1  1:1-9:1 6 Tebuthiuron 1:384-3:11:128-1:1  1:48-1:6 6 Tefuryltrione  1:42-27:1 1:14-9:1  1:5-2:1 6Tembotrione  1:31-37:1  1:10-13:1  1:3-3:1 6 Tepraloxydim  1:25-45:1 1:8-15:1  1:3-3:1 6 Terbacil 1:288-4:1 1:96-2:1 1:36-1:4 6Terbuthylazine 1:857-2:1 1:285-1:3  1:107-1:12 6 Terbutryn 1:192-6:11:64-2:1 1:24-1:3 6 Thenylchlor  1:85-14:1 1:28-5:1 1:10-1:2 6 Thiazopyr1:384-3:1 1:128-1:1  1:48-1:6 6 Thiencarbazone   1:3-336:1   1:1-112:1 2:1-21:1 6 Thifensulfuron-methyl   1:5-224:1  1:1-75:1  1:1-14:1 6Tiafenacil  1:17-68:1  1:5-23:1  1:2-5:1 6 Thiobencarb 1:768-2:11:256-1:2   1:96-1:11 6 Topramezone   1:6-168:1  1:2-56:1  1:1-11:1 6Tralkoxydim  1:68-17:1 1:22-6:1  1:8-2:1 6 Triallate 1:768-2:11:256-1:2   1:96-1:11 6 Triasulfuron   1:5-224:1  1:1-75:1  1:1-14:1 6Triaziflam 1:171-7:1 1:57-3:1 1:21-1:3 6 Tribenuron-methyl   1:3-336:1  1:1-112:1  2:1-21:1 6 Triclopyr 1:192-6:1 1:64-2:1 1:24-1:3 6Trifloxysulfuron   1:2-420:1   1:1-140:1  2:1-27:1 6 Trifluralin1:288-4:1 1:96-2:1 1:36-1:4 6 Triflusulfuron-methyl  1:17-68:1  1:5-23:1 1:2-5:1 6 Tritosulfuron  1:13-84:1  1:4-28:1  1:1-6:1

Table A2 is constructed the same as Table A1 above except that entriesbelow the “Component (a)” column heading are replaced with therespective Component (a) Column Entry shown below. Compound 2 in theComponent (a) column is identified in Index Table A. Thus, for example,in Table A2 the entries below the “Component (a)” column heading allrecite “Compound 1” (i.e. Compound 1 identified in Index Table A), andthe first line below the column headings in Table A2 specificallydiscloses a mixture of Compound 1 with 2,4-D. Tables A3 through A18 areconstructed similarly.

Table Number Component (a) Column Entries A2 Compound 1 A3 Compound 2 A4Compound 3 A5 Compound 4 A6 Compound 5 A7 Compound 7 A8 Compound 8 A9Compound 9 A10 Compound 10 A11 Compound 11 A12 Compound 12 A13 Compound13 A14 Compound 14 A15 Compound 15 A16 Compound 16 A17 Compound 17 A18Compound 18 A19 Compound 19 A20 Compound 20 A21 Compound 21 A22 Compound22

Preferred for better control of undesired vegetation (e.g., lower userate such as from synergism, broader spectrum of weeds controlled, orenhanced crop safety) or for preventing the development of resistantweeds are mixtures of a compound of this invention with a herbicideselected from the group consisting of chlorimuron-ethyl, nicosulfuron,mesotrione, thifensulfuron-methyl, flupyrsulfuron-methyl, tribenuron,pyroxasulfone, pinoxaden, tembotrione, pyroxsulam, metolachlor andS-metolachlor.

The following Tests demonstrate the control efficacy of the compounds ofthis invention against specific weeds. The weed control afforded by thecompounds is not limited, however, to these species. See Index Table Afor compound descriptions. The following abbreviations are used in theIndex Table which follows: CF₃ is trifluoromethyl and Ph is phenyl. (R)or (S) denotes the absolute chirality of the asymmetric carbon center.The abbreviation “(d)” indicates that the compound appeared to decomposeon melting. The abbreviation “Cmpd. No.” stands for “Compound Number”.The abbreviation “Ex.” stands for “Example” and is followed by a numberindicating in which example the compound is prepared.

INDEX TABLE A ⁽¹⁾

Cmpd. No. Q¹ Q² R⁵ m.p. (° C.)  1 Ph(4-F) Ph(2-Cl) H 173-175  2 Ph(4-F)Ph(2-F) H 184-186  3 Ph(3,4-di-F) Ph(2-Cl) H *  4 Ph(3,4-di-F) Ph(2-F)H *  5 Ph(4-F) Ph(2-CH₃) H 172-174 6 (Ex. 1) Ph(4-F) Ph(2-CF₃) H144-146**  7 Ph(4-CF₃) Ph(2,3-di-F) H 188-191  8 Ph(4-CF₃) Ph(2-F) H180-183  9 Ph(4-CF₃) Ph(2-CF₃) H 142-145 10 Ph(4-CF₃) Ph(3-F,2-CF₃) H146-150 11 Ph(3-CF₃) Ph(2-F) H 92-95 12 Ph(3-CF₃) Ph(2,3-di-F) H 103-10713 Ph(3-CF₃) Ph(3-F,2-CF₃) H 99-103 14 Ph(3-CF₃) Ph(2-CF₃) H 73-75 15Ph(4-F,3-CF₃) Ph(2,3-di-F) H 133-136 16 Ph(4-F,3-CF₃) Ph(2-F) H 154-15717 Ph(4-F,3-CF₃) Ph(2-CF₃) H 104-106 18 Ph(4-F,3-CF₃) Ph(3-F,2-CF₃) H118-121 19 Ph(4-F) Ph(2-F) CH₃ 104-108 20 Ph(4-F) Ph(2-F) CH₃ 152-156 21Ph(4-F) Ph(2-CF₃) CH₃ 382 (M + H) 22 Ph(4-F) Ph(2,3-di-F) CH₃ 96-100 ⁽¹⁾Substituents in the 3 and 4 positions of the butyrolactone ring, i.e.C(O)N(Q²)H and Q¹, respectively, are predominately in the transconfiguration. In some instances the presence of minor amounts of thecis isomer can be detected by NMR. In this structure of Formula 1, eachR², R³ and R⁴ is H. * See Index Table B for ¹H NMR data. **See SynthesisExample for ¹H NMR data.

INDEX TABLE B Cmpd. No. ¹H NMR Data (DMSO-d₆ solution unless indicatedotherwise)^(a) 3 δ 10.03 (s, 1H), 7.72-7.69 (m, 1H), 7.64-7.59 (m, 1H),7.51-7.43 (m, 2H), 7.35-7.19 (m, 3H), 4.74-4.70 (t, J = 16.4 Hz, 1H),4.32-4.19 (m, 3H). 4 δ 10.23 (s, 1H), 7.91-7.86 (m, 1H), 7.63-7.57 (m,1H), 7.49-7.42 (m, 1H), 7.29-7.16 (m, 4H), 4.74-4.70 (t, J = 8.4 Hz,1H), 4.35-4.22 (m, 3H). ^(a) ¹H NMR data are in ppm downfield fromtetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet,(t)-triplet, (m)-multiplet.

Biological Examples of the Invention Test A

Seeds of plant species selected from barnyardgrass (Echinochloacrus-galli), crabgrass (large crabgrass, Digitaria sanguinalis), kochia(Kochia scoparia), ragweed (common ragweed, Ambrosia elatior),morningglory (Ipomoea spp.), velvetleaf (Abutilon theophrasti),ryegrass, Italian (Italian ryegrass, Lolium multiflorum), foxtail, giant(giant foxtail, Setaria faberii), wheat (Triticum aestivum), corn (Zeamays), and pigweed (Amaranthus retroflexus), were planted into a blendof loam soil and sand and treated preemergence with a directed soilspray using test chemicals formulated in a non-phytotoxic solventmixture which included a surfactant.

At the same time, plants selected from these crop and weed species andalso blackgrass (Alopecurus myosuroides), and galium (catchweedbedstraw, Galium aparine), were planted in pots containing the sameblend of loam soil and sand and treated with postemergence applicationsof test chemicals formulated in the same manner. Plants ranged in heightfrom 2 to 10 cm and were in the one- to two-leaf stage for thepostemergence treatment. Treated plants and untreated controls weremaintained in a greenhouse for approximately 10 d, after which time alltreated plants were compared to untreated controls and visuallyevaluated for injury. Plant response ratings, summarized in Table A, arebased on a 0 to 100 scale where 0 is no effect and 100 is completecontrol. A dash (-) response means no test result.

TABLE A Compounds 1000 g ai/ha 1 2 4 5 6 Postemergence Barnyardgrass 200 70 50 20 Corn 0 0 — 0 0 Crabgrass 60 40 90 80 80 Foxtail, Giant 40 070 60 80 Morningglory 0 0 0 0 0 Pigweed 20 0 0 0 0 Velvetleaf 0 0 0 0 0Wheat 0 0 0 0 0 Compounds 500 g ai/ha 3 7 8 9 10 11 12 13 14 15 16 17 1819 Postemergence Barnyardgrass 0 20  20  0 0 40  40  0 20  70 50  0 080  Blackgrass — 0 0 0 0 0 0 0 30  20 0 0 0 0 Corn — 0 0 0 0 0 0 0 0 200 0 0 0 Crabgrass 70  — — — — — — — — — — — — — Foxtail, Giant 60  50 40  70  70  60  70  40  70  70 40  20  30  40  Galium — 0 0 0 0 0 0 030  20 0 0 0 0 Kochia — 0 0 0 0 0 0 0 0  0 0 0 0 0 Morningglory 0 — — —— — — — — — — — — — Pigweed 0 0 0 0 0 0 0 0 0  0 0 0 0 0 Ragweed — 0 0 00 0 0 0 0  0 0 0 0 0 Ryegrass, Italian — 0 0 0 0 0 0 0 0 20 0 0 0 0Velvetleaf 0 — — — — — — — — — — — — — Wheat 0 0 0 0 0 20  0 0 0 20 0 00 0 Compounds 500 g ai/ha 20 21 Postemergence Barnyardgrass 0 30 Blackgrass 0 30  Corn 0 0 Crabgrass — — Foxtail, Giant 0 0 Galium 0 30 Kochia 0 0 Morningglory — — Pigweed 0 0 Ragweed 0 40  Ryegrass, Italian0 0 Velvetleaf — — Wheat 0 0 Compounds 125 g ai/ha 3 7 8 9 10 11 12 1314 15 16 17 18 19 Postemergence Barnyardgrass 0 0 0 0 0 10  40  0 0 30 20  0 0 20  Blackgrass — 0 0 0 0 0 0 0 0 0 0 0 0 0 Corn — 0 0 0 0 0 0 00 0 0 0 0 0 Crabgrass 60  — — — — — — — — — — — — — Foxtail, Giant 50 20  20  30  30  20  30  20  20  30  20  0 0 20  Galium — 0 0 0 0 0 0 0 00 0 0 0 0 Kochia — 0 0 0 0 0 0 0 0 0 0 0 0 0 Morningglory 0 — — — — — —— — — — — — — Pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ragweed — 0 0 0 0 0 00 0 0 0 0 0 0 Ryegrass, Italian — 0 0 0 0 0 0 0 0 0 0 0 0 0 Velvetleaf 0— — — — — — — — — — — — — Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 CompoundsCompound 125 g ai/ha 20 21 22 31 g ai/ha 22 Postemergence Barnyardgrass0 0 90  Barnyardgrass 40 Blackgrass 0 0 0 Blackgrass 0 Corn 0 0 0 Corn 0Crabgrass — — — Foxtail, Giant 30 Foxtail, Giant 0 0 60  Galium 0 Galium0 0 20  Kochia 0 Kochia 0 0 0 Pigweed 0 Morningglory — — — Ragweed 0Pigweed 0 0 0 Ryegrass, Italian 20 Ragweed 0 0 0 Wheat 0 Ryegrass,Italian 0 0 20  Velvetleaf — — — Wheat 0 0 0 Compounds 1000 g ai/ha 1 24 5 6 Preemergence Barnyardgrass 0 30 70 60 20 Corn 0 0 0 0 0 Crabgrass70 80 90 80 80 Foxtail, Giant 40 50 80 70 80 Morningglory 0 0 0 0 0Pigweed 0 0 0 0 0 Velvetleaf 0 0 0 0 0 Wheat 0 0 0 0 0 Compounds 500 gai/ha 3 7 8 9 10 11 12 13 14 15 16 17 18 19 Preemergence Barnyardgrass30  30  20  0 0 80  30 0 20 70 60  0 0 90  Corn 0 — — — — — — — — — — —— — Crabgrass 50  — — — — — — — — — — — — — Foxtail, Giant 80  80  40 80  50  80  60 70  90 90 80  60  40  90  Kochia — 0 0 20  0 0 20 0 20  00 0 0 0 Morningglory 0 — — — — — — — — — — — — — Pigweed 0 0 0 0 0 0  00  0  0 0 0 0 20  Ragweed — 0 0 0 0 0  0 0  0  0 0 0 0 0 Ryegrass,Italian — 0 0 20  0 0 20 0 20 40 0 0 0 0 Velvetleaf 0 — — — — — — — — —— — — — Wheat 0 — — — — — — — — — — — — — Compounds 125 g ai/ha 3 7 8 910 11 12 13 14 15 16 17 18 19 Preemergence Barnyardgrass 0 0 0 0 0 30 20  0 20  40  30  0 0 30  Corn 0 — — — — — — — — — — — — — Crabgrass 40 — — — — — — — — — — — — — Foxtail, Giant 70  30  20  30  40  70  30  40 70  70  50  20  0 20  Kochia — 0 0 0 0 0 0 0 0 0 0 0 0 — Morningglory 0— — — — — — — — — — — — — Pigweed 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Ragweed —0 0 0 0 0 0 0 0 0 0 0 0 0 Ryegrass, Italian — 0 0 0 0 0 0 0 0 0 0 0 0 0Velvetleaf 0 — — — — — — — — — — — — — Wheat 0 — — — — — — — — — — — — —

Test B

Plant species in the flooded paddy test selected from rice (Oryzasativa), sedge, umbrella (small-flower umbrella sedge, Cyperusdifformis), ducksalad (Heteranthera limosa), and barnyardgrass(Echinochloa crus-galli) were grown to the 2-leaf stage for testing. Attime of treatment, test pots were flooded to 3 cm above the soilsurface, treated by application of test compounds directly to the paddywater, and then maintained at that water depth for the duration of thetest. Treated plants and controls were maintained in a greenhouse for 13to 15 d, after which time all species were compared to controls andvisually evaluated. Plant response ratings, summarized in Table B, arebased on a scale of 0 to 100 where 0 is no effect and 100 is completecontrol. A dash (-) response means no test result.

TABLE B Compounds 1000 g ai/ha 7 8 9 10 Flood Barnyardgrass 0 0 0 0Ducksalad 40 30 30 25 Rice 0 0 0 0 Sedge, Umbrella 0 0 0 0 Compounds 500g ai/ha 11 12 13 14 15 16 17 18 Flood Barnyardgrass 0 0 0 0 0 0 0 0Ducksalad 0 0 0 0 0 0 0 0 Rice 0 0 0 0 0 0 0 0 Sedge, Umbrella 0 0 0 0 00 0 0 Compounds 250 g ai/ha 3 4 6 7 8 9 10 19 20 21 22 FloodBarnyardgrass 0 20 0 0 0 0 0 0 0 90 0 Ducksalad 0 0 0 30 30 30 20 0 0 900 Rice 0 15 0 0 0 0 0 0 0 30 20 Sedge, Umbrella 0 0 0 0 0 0 0 0 0 0 0

What is claimed is:
 1. A compound selected from Formula 1, N-oxides andsalts thereof,

wherein Q¹ is a phenyl ring or a naphthalenyl ring system, each ring orring system optionally substituted with up to 5 substituentsindependently selected from R⁷; or a 5- to 6-membered fully unsaturatedheterocyclic ring or an 8- to 10-membered heteroaromatic bicyclic ringsystem, each ring or ring system containing ring members selected fromcarbon atoms and 1 to 4 heteroatoms independently selected from up to 2O, up to 2 S and up to 4 N atoms, wherein up to 3 carbon ring membersare independently selected from C(═O) and C(═S), and the sulfur atomring members are independently selected from S(═O)_(u)(═NR⁸)_(v), eachring or ring system optionally substituted with up to 5 substituentsindependently selected from R⁷ on carbon atom ring members and selectedfrom R⁹ on nitrogen atom ring members; Q² is a phenyl ring or anaphthalenyl ring system, each ring or ring system optionallysubstituted with up to 5 substituents independently selected from R¹⁰;or a 5- to 6-membered fully unsaturated heterocyclic ring or an 8- to10-membered heteroaromatic bicyclic ring system, each ring or ringsystem containing ring members selected from carbon atoms and 1 to 4heteroatoms independently selected from up to 2 O, up to 2 S and up to 4N atoms, wherein up to 3 carbon ring members are independently selectedfrom C(═O) and C(═S), and the sulfur atom ring members are independentlyselected from S(═O)_(u)(═NR⁸)_(v), each ring or ring system optionallysubstituted with up to 8 substituents independently selected from R¹⁰ oncarbon atom ring members and selected from R¹¹ on nitrogen atom ringmembers; Y¹ and Y² are each independently O, S or NR⁶; R¹ is H, hydroxy,amino, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₂-C₈alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylcarbonyl, C₂-C₈haloalkylcarbonyl, C₄-C₁₀ cycloalkylcarbonyl, C₂-C₈ alkoxycarbonyl,C₂-C₈ haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆haloalkylsulfinyl, C₃-C₈ cycloalkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆haloalkylsulfonyl, C₃-C₈ cycloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl,C₂-C₈ dialkylaminosulfonyl, C₃-C₁₀ trialkylsilyl or G¹; R² and R³ areeach independently H, halogen, hydroxy, C₁-C₄ alkyl, C₁-C₄ haloalkyl orC₁-C₄ alkoxy; or R² and R³ are taken together with the carbon atom towhich they are bonded to form a C₃-C₇ cycloalkyl ring; R⁴ and R⁵ areeach independently H, halogen, hydroxy, C₁-C₄ alkyl or C₁-C₄ alkoxy;each R⁶ is independently H, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄alkoxy, C₁-C₄ haloalkoxy, —(C═O)CH₃ or —(C═O)CF₃; each R⁸ isindependently H, cyano, C₂-C₃ alkylcarbonyl or C₂-C₃ haloalkylcarbonyl;each R⁷ and R¹⁰ is independently halogen, cyano, nitro, C₁-C₈ alkyl,C₁-C₄ cyanoalkyl, C₁-C₄ cyanoalkoxy, C₁-C₈ haloalkyl, C₁-C₈ nitroalkyl,C₂-C₈ alkenyl, C₂-C₈ haloalkenyl, C₂-C₈ nitroalkenyl, C₂-C₈ alkynyl,C₂-C₈ haloalkynyl, C₄-C₁₀ cycloalkylalkyl, C₄-C₁₀ halocycloalkylalkyl,C₅-C₁₂ alkylcycloalkylalkyl, C₅-C₁₂ cycloalkylalkenyl, C₅-C₁₂cycloalkylalkynyl, C₃-C₈ cycloalkyl, C₃-C₈ halocycloalkyl, C₄-C₁₀alkylcycloalkyl, C₆-C₁₂ cycloalkylcycloalkyl, C₃-C₈ cycloalkenyl, C₃-C₈halocycloalkenyl, C₂-C₈ alkoxyalkyl, C₂-C₈ haloalkoxyalkyl, C₄-C₁₀cycloalkoxyalkyl, C₃-C₁₀ alkoxyalkoxyalkyl, C₂-C₈ alkylthioalkyl, C₂-C₈alkylsulfinylalkyl, C₂-C₈ alkylsulfonylalkyl, C₂-C₈ alkylaminoalkyl,C₂-C₈ haloalkylaminoalkyl, C₄-C₁₀ cycloalkylaminoalkyl, C₃-C₁₀dialkylaminoalkyl, —CHO, C₂-C₈ alkylcarbonyl, C₂-C₈ haloalkylcarbonyl,C₄-C₁₀ cycloalkylcarbonyl, —C(═O)OH, C₂-C₈ alkoxycarbonyl, C₂-C₈haloalkoxycarbonyl, C₄-C₁₀ cycloalkoxycarbonyl, C₅-C₁₂cycloalkylalkoxycarbonyl, —C(═O)NH₂, C₂-C₈ alkylaminocarbonyl, C₄-C₁₀cycloalkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₁-C₈ alkoxy,C₁-C₈ haloalkoxy, C₂-C₈ alkoxyalkoxy, C₂-C₈ haloalkoxyalkoxy, C₂-C₈alkenyloxy, C₂-C₈ haloalkenyloxy, C₃-C₈ alkynyloxy, C₃-C₈haloalkynyloxy, C₃-C₈ cycloalkoxy, C₃-C₈ halocycloalkoxy, C₄-C₁₀cycloalkylalkoxy, C₃-C₁₀ alkylcarbonylalkoxy, C₂-C₈ alkylcarbonyloxy,C₂-C₈ haloalkylcarbonyloxy, C₄-C₁₀ cycloalkylcarbonyloxy, C₁-C₈alkylsulfonyloxy, C₁-C₈ haloalkylsulfonyloxy, C₁-C₈ alkylthio, C₁-C₈haloalkylthio, C₃-C₈ cycloalkylthio, C₁-C₈ alkylsulfinyl, C₁-C₈haloalkylsulfinyl, C₁-C₈ alkylsulfonyl, C₁-C₈ haloalkylsulfonyl, C₃-C₈cycloalkylsulfonyl, formylamino, C₂-C₈ alkylcarbonylamino, C₂-C₈haloalkylcarbonylamino, C₂-C₈ alkoxycarbonylamino, C₁-C₆alkylsulfonylamino, C₁-C₆ haloalkylsulfonylamino, —SF₅, —SCN, SO₂NH₂,C₃-C₁₂ trialkylsilyl, C₄-C₁₂ trialkylsilylalkyl, C₄-C₁₂trialkylsilylalkoxy or G²; or two adjacent R⁷ are taken together alongwith the carbon atoms to which they are bonded to form a C₃-C₇cycloalkyl ring; or two adjacent R¹⁰ are taken together along with thecarbon atoms to which they are bonded to form a C₃-C₇ cycloalkyl ring;each R⁹ and R¹¹ is independently cyano, C₁-C₃ alkyl, C₂-C₃ alkenyl,C₂-C₃ alkynyl, C₃-C₆ cycloalkyl, C₂-C₃ alkoxyalkyl, C₁-C₃ alkoxy, C₂-C₃alkylcarbonyl, C₂-C₃ alkoxycarbonyl, C₂-C₃ alkylaminoalkyl or C₃-C₄dialkylaminoalkyl; each G¹ is independently phenyl, phenylmethyl,pyridinylmethyl, phenylcarbonyl, phenylcarbonyl(C₁-C₄ alkyl), phenoxy,phenylethynyl, phenylsulfonyl, or a 5- or 6-membered heteroaromaticring, each optionally substituted on ring members with up to 5substituents independently selected from R¹²; each G² is independentlyphenyl, phenylmethyl, pyridinylmethyl, phenylcarbonyl,phenylcarbonyl(C₁-C₄ alkyl), phenoxy, phenylethynyl, phenylsulfonyl,pyridinyloxy, or a 5- or 6-membered heteroaromatic ring, each optionallysubstituted on ring members with up to 5 substituents independentlyselected from R¹³; each R¹² and R¹³ is independently halogen, cyano,hydroxy, amino, nitro, —CHO, —C(═O)OH, —C(═O)NH₂, —SO₂NH₂, C₁-C₆ alkyl,C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₂-C₈ alkylcarbonyl,C₂-C₈ haloalkylcarbonyl, C₂-C₈ alkoxycarbonyl, C₄-C₁₀cycloalkoxycarbonyl, C₅-C₁₂ cycloalkylalkoxycarbonyl, C₂-C₈alkylaminocarbonyl, C₃-C₁₀ dialkylaminocarbonyl, C₁-C₆ alkoxy, C₁-C₆haloalkoxy, C₂-C₈ alkylcarbonyloxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ haloalkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylaminosulfonyl, C₂-C₈dialkylaminosulfonyl, C₃-C₁₀ trialkylsilyl, C₁-C₆ alkylamino, C₂-C₈dialkylamino, C₂-C₈ alkylcarbonylamino, C₁-C₆ alkylsulfonylamino,phenyl, pyridinyl or thienyl; and each u and v are independently 0, 1 or2 in each instance of S(═O)_(u)(═NR⁸)_(v), provided that the sum of uand v is 0, 1 or
 2. 2. The compound of claim 1 wherein each R⁷ and R¹⁰is independently halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl,C₂-C₄ alkenyl, C₂-C₄ haloalkenyl C₂-C₄ alkynyl, C₂-C₄ haloalkynyl, C₁-C₄nitroalkyl, C₂-C₄ nitroalkenyl, C₂-C₄ alkoxyalkyl, C₂-C₄haloalkoxyalkyl, C₃-C₄ cycloalkyl, C₃-C₄ halocycloalkyl,cyclopropylmethyl, methylcyclopropyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy,C₂-C₄ alkenyloxy, C₂-C₄ haloalkenyloxy, C₃-C₄ alkynyloxy, C₃-C₄haloalkynyloxy, C₃-C₄ cycloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio,C₁-C₄ alkylsulfinyl, C₁-C₄ haloalkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄haloalkylsulfonyl, hydroxy, formyl, C₂-C₄ alkylcarbonyl, C₂-C₄alkylcarbonyloxy, C₁-C₄ alkylsulfonyloxy, C₁-C₄ haloalkylsulfonyloxy,amino, C₁-C₄ alkylamino, C₂-C₄ dialkylamino, formylamino, C₂-C₄alkylcarbonylamino, —SF₅, —SCN, C₃-C₄ trialkylsilyl,trimethylsilylmethyl or trimethylsilylmethoxy; and each R⁹ and R¹¹ isindependently C₁-C₂ alkyl or C₂-C₃ alkoxycarbonyl.
 3. The compound ofclaim 2 wherein Y¹ is O; Y² is O; R¹ is H; R² is H; R³ is H; R⁴ is H;and R⁵ is H or CH₃.
 4. The compound of claim 3 wherein Q¹ is a phenylring substituted with 1 to 3 substituents independently selected fromR⁷; and Q² is a phenyl ring substituted with 1 to 3 substituentsindependently selected from R¹⁰.
 5. The compound of claim 4 wherein eachR⁷ is independently halogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl C₁-C₄alkoxy or C₁-C₄ haloalkoxy; and each R¹⁰ is independently halogen,cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl or C₁-C₄ alkylsulfonyl.
 6. Thecompound of claim 5 wherein Q¹ is a phenyl ring substituted with 1substituent selected from R⁷ at the para position or substituted with 2substituents independently selected from R⁷ wherein one substituent isat the para position and the other substituent is at a meta position;and Q² is a phenyl ring substituted with 1 substituent selected from R¹⁰at an ortho position or substituted with 2 substituents independentlyselected from R¹⁰ wherein one substituent is at an ortho position andthe other substituent is at the adjacent meta position.
 7. The compoundof claim 6 wherein each R⁷ is independently F or CF₃; and each R¹⁰ is F.8. The compound of claim 1 selected from the group consisting of4-(4-fluorophenyl)tetrahydro-2-oxo-N-[2-(trifluoromethyl)phenyl)]-3-furancarboxamide;(3R,4S)-4-(4-fluorophenyl)tetrahydro-2-oxo-N-[2-(trifluoromethyl)phenyl)]-3-furancarboxamide;and(3S,4R)-4-(4-fluorophenyl)tetrahydro-2-oxo-N-[2-(trifluoromethyl)phenyl)]-3-furancarboxamide.9. A herbicidal composition comprising a compound of claim 1 and atleast one component selected from the group consisting of surfactants,solid diluents and liquid diluents.
 10. A herbicidal compositioncomprising a compound of claim 1, at least one additional activeingredient selected from the group consisting of other herbicides andherbicide safeners, and at least one component selected from the groupconsisting of surfactants, solid diluents and liquid diluents.
 11. Aherbicidal mixture comprising (a) a compound of claim 1, and (b) atleast one additional active ingredient selected from (b1) through (b16)and salts of compounds of (b1) through (b16).
 12. A method forcontrolling the growth of undesired vegetation comprising contacting thevegetation or its environment with a herbicidally effective amount of acompound of claim 1.